By Kelsey Fox
There is something characteristically American about the idea of Main Street. Whether a place for the locals to hang out, or the go-to destination of visitors to town, Main Street is oftentimes the heart and soul of a city or town. That is especially true in the case of the 50 small towns on this list.
Each town on this list has fewer than 60,000 residents (according to the 2010 census) and at least one notable attraction. The towns were chosen and ranked based upon the following.
- Inclusion on a major register, such as the National Register of Historic Places, National Parks, National Historic Landmarks, etc. (1 point per list)
- Category of downtown attractions (restaurants, wineries, antique stores, art galleries, etc.). (1 point per notable category)
- Notable and historic places (1 point each)
- A national ranking of some kind (1 point each)
50. Georgetown, Texas
The picture perfect main street is just part of what makes Georgetown’s downtown the “quintessential Texas downtown.” Georgetown Square is an ever lively gathering place ringed with lovingly restored buildings originally built in the late 1800s and early 1900s. Today, these buildings are mom-and-pop shops, art galleries, and decades-old restaurants where staff and owners personally greet locals by name. In more ways than one, tiny Georgetown gives visitors a unique glimpse of an earlier era.
49. Corinth, Mississippi
Fillmore Street, located in downtown Corinth, Mississippi, is a charming blend of everything old and new. The small town’s main street is flush with historic buildings turned boutiques and art galleries that reportedly “always keep their doors propped open.” Fillmore’s hungry visitors will also find a wide range of locally owned restaurants and coffee houses. One particular Corinth gem is the Generals’ Quarters Inn, an old Victorian home now operating as a bed and breakfast. Take a leisurely stroll along Fillmore Street, and you’ll understand why Parade Magazine called Corinth one of “America’s Best Small Towns.”
48. Elkin, North Carolina
Tiny Elkin, North Carolina is an outdoorsman’s heaven with plenty of hiking, canoeing, birding, and cycling options. Downtown Elkin accomplishes the unique task of making the small town feel much larger than its population of just over 4,000. Visitors have a wide variety of theaters, restaurants and cafes, and mom-and-pop shops to choose from, not the mention the number of historic buildings and sites that would fascinate anyone. Visitors can even catch a wine tasting tour that trails through the nearby wine region.
47. Port Townsend, Washington
Port Townsend, Washington was founded in the 19th century by those expecting a shipping boom. Unfortunately, Port Townsend proved to be on the wrong side of Puget Sound when the railroads connected to Seattle ultimately appeared, so the small town has had to compensate in charm and appeal. And compensate it has. Today, Port Townsend is known as one of the premiere arts centers in Washington. Much of its downtown main street is designed in high Victorian style, making it a must-see for architecture buffs. The Hastings Building, with its blue and white color scheme and characteristic bay windows, is the most photographed landmark in the downtown. Also worth visiting is the Rose Theater. Originally built in 1907 and used as a vaudeville theater, the Rose has been carefully restored and now shows new movies in what must be the most beautiful setting imaginable.
46. Cazenovia, New York
Cazenovia, New York is a small town located in central New York. Surrounded by elegant countryside, many of its 2,700 residents are active in the horse world (some even professionally), and so Cazenovia itself boasts a decidedly sophisticated equestrian air. Its downtown is located along the shores of Cazenovia Lake, and walking along its main street of Albany Street is like taking a stroll back in time. Albany is lined with everything from sidewalk cafes, to quaint antique shops, to independent bookstores, to chic boutiques. Anyone visiting Albany Street for the first time shouldn’t miss a visit to Brae Loch Inn, the famous Scottish-themed inn and restaurant which is famous for its Sunday brunch.
45. Buckhannon, West Virginia
Buckhannon, located in the heart of West Virginia, was recently named by the Huffington Post as one of the “Coolest Small Towns” in America. Its Main Street is full of artsy boutiques and specialty shops, plus a fair share of art galleries and antique dealers. An official historic district, wanderers are sure to be impressed by the turn-of-the-century architecture and buildings of historical significance. Surrounding Buckhannon is a nature and wildlife paradise for any hiker, cyclist, birder, or outdoorsman to enjoy.
44. Williamsburg, Virginia
Williamsburg, Virginia might just have the most unique downtown main street of any town on this list. The 301-acre downtown area is a living museum, and reenacts life during the American Revolution 365 days a year (in fact, Williamsburg’s historic reenactment is considered the best in the world). Visitors along the main street are sure to enjoy speaking with the costumed actors and visiting the meticulously detailed, Colonial-era shops and restaurants. Visit in October and take in the annual An Occasion for the Arts. Interestingly, located within only a few miles of downtown Williamsburg is Jamestown, the first permanent English settlement in what would become the United States.
43. Heber City, Utah
With plenty of options for boating, golfing, horseback riding, skiing, hiking, and biking, Heber City, Utah has long been a popular vacation destination. Downtown, Heber City’s main street is a thriving community of art and culture. Festivals and special events occur almost on a weekly basis throughout the year, and include theatrical performances, art shows, and Native American celebrations. Visitors flock to Heber City’s main streets during the annual Wasatch County Fair, a week-long spectacle of parades, carnival rides, a beauty pageant, rodeo, and a demolition derby.
42. Rockland, Maine
Rockland, Main is a quaint New England seaside village that also happens to have a wicked trendy art scene. Galleries, boutiques, bookstores, shops, and restaurants are plentiful on the picturesque Main Street. Tour the Main Lighthouse Museum for a glimpse of Rockland’s typical New England history, or catch one of the many concerts held downtown. And like any New England seaside town, there is delicious lobster available at any meal time in most of the Main Street restaurants.
41. Excelsior, Minnesota
The heart of tiny Excelsior, Minnesota is the downtown main street, Water Street. Water Street is lined with restaurants, cafes, boutiques, bookstores, antique shops, and anything else in which a local or visitor may be interested. Most impressively, Water Street ultimately leads pedestrians to what is known as The Commons, a beautiful 13-acre park separating the town from Lake Minnetonka. Grab dinner on Water Street, then enjoy an evening on the beach!
40. Littleton, New Hampshire
Located in northern New Hampshire, Littleton sits on the Ammonoosuc River. The town’s Main Street is vibrant and self-sufficient, offering both visitors and locals just about anything one could possibly need. Main Street is especially appealing to those interested in architecture, as its buildings are a unique mix of Modernism and 1850s-era Neoclassicism. Main Street gems include Thayers Inn, the world’s longest candy counter at Chutters, and Just L Modern Antiques, which specializes in midcentury modern, “Mad Men” era antiques.
39. York, Pennsylvania
The last big department store on Market Street in York, Pennsylvania closed in 1978, and since then, the little town with a population of just under 50,000 has worked hard to create a charming downtown. Indeed, Market Street is now flush with old buildings restored into locally owned shops. Most of said buildings are fine examples of Late Victorian or Classical Revival Style architecture. Market Street has been a mecca for food vendors and quick meals since 1754. To honor this legacy, many local businesses and restaurants stay open late on the First Friday of each month. On any other day, however, Market has over 25 restaurants and lunch counters to choose from.
38. Placerville, California
Founded during the 1849 gold rush, Placerville, California’s downtown main street has been beautifully restored into a popular stopping point for locals and tourists alike. Must-dos include a visit to the iconic bell tower that stands in the middle of town, and a step inside the 160-year old Placerville Hardware Store. Visit “The Old Hangtown” at the right time and you might stumble into Placerville’s monthly festival of sorts, complete with stagecoach rides. Fans of 20th century art might find it interesting that Placerville was once home to the late Thomas Kinkade, who often depicted its welcoming setting in his paintings.
37. Natchitoches, Louisiana
Tiny Natchitoches, Louisiana is a quiet town originally founded in 1714 — four whole years before anyone thought of settling four hours southeast in what would become New Orleans. Natchitoches’ main drag is Front Street, so named because it faces the Cane River. Front Street is lined with live oak trees and winsome buildings with balconies and cast iron gates. Movie buffs may recognize the street, which oozes a uniquely southern feel, as one of the main filming locations for Steel Magnolias. Visitors must visit the restaurant Lasyone’s Meat Pie, which serves an empanada-type dish stuffed with beef and pork — a local Civil War-era favorite.
36. Rome, Georgia
Broad Street, the main street of Rome, Georgia, has become the perfect example of small-town revitalization. Since the 1970s, Rome’s residents have invested millions of dollars in the restoration and renovation of more than 120 buildings, including the entire central business district. Broad Street is now the perfect place for a stroll, where walkers will enjoy the view of charming Victorian-style homes and churches, all lovingly restored. The Municipal Building is also worth checking out, if only for the bronze Romulus and Remus statue that graces the front. A classic symbol of Rome, Italy, it was presented to the town in 1929 by an Italian governor.
35. Berlin, Maryland
Berlin, Maryland boasts a picturesque downtown main street that might look familiar to those who have seen films like “Tuck Everlasting” or “Runaway Bride.” Tiny Berlin, home to a population of just over 4,500 people, was recently named by the Huffington Post as one of America’s “Coolest Small Towns.” Downtown hosts a number of events throughout the calendar year, including weekly farmers markets, the Berlin Fiddlers’ Convention, a Victorian Christmas, and even annual bathtub races! Additionally, Berlin’s entire downtown district has been honored with a place on the National Register of Historic Places.
34. Steamboat Springs, Colorado
Daytime in Steamboat Springs, Colorado may be spent skiing the “champagne powder” at some of the best ski resorts in the country, but evenings are spent downtown. Steamboat Springs’ thoroughly modern downtown main streets cater to pedestrians and tourists. In fact, it’s downtown that celebrates that other thing Steamboat Springs is famous for — music. Halls for the symphony, chamber orchestra, and opera are all located downtown, while free concerts are often held outside. In summertime, people from all over flock downtown for the world-class music festival which brings together everything from rock artists to first-chair musicians.
33. Paducah, Kentucky
In 2000, Paducah, Kentucky made the risky move of offering incentives to artists willing to relocate to downtown Paducah. Today, the small Kentucky town is a thriving community built around the arts. Besides the many Victorian houses and art galleries lining the town’s main street, art-loving wanderers will find the series of Floodwall Murals depicting events in local history and the rotating exhibits of the National Quilt Museum. Thanks to Paducah’s Arts a la Carte program, many artists set up workstations directly on the sidewalk for the enjoyment of passersby. A number of festivals — both art themed and otherwise — also occur in Paducah throughout the year.
32. Woodstock, Vermont
Woodstock, Vermont is an upscale community where the well-off population of 3,200 live in quiet life in characteristically large homes. Such sophistication extends to downtown Center Street and stems from Woodstock’s prosperous industrial history. Center Street, with its boutiques, bakeries, and restaurants, actually divides downtown and The Green, an appealing oval park, from a picturesque covered bridge and a group of colonnaded houses beyond. A wander through the park is a must-do, as is a visit to Billings Farm and Museum, a lovingly maintained farm. Located at the end of Center Street and the edge of The Green, Billings Farm showcases in a fascinating way what was the state of artistic architecture in the 1870s.
31. Montpelier, Vermont
With a population of less than 8,000 people, Montpelier, Vermont is one of those sought-after communities in which everyone seems to know everyone else. The downtown feels especially close knit. Wander along Main Street and you’ll find locally owned cafes, bookstores, and shops with their doors propped open and friendly staff inside. Despite this quaintness, Montpelier also attracts major foodies from all parts of the country. Main Street and nearby State Street are home to a number of craft beer bars and top-ranked restaurants of all varieties.
30. Silver City, New Mexico
The old mining town of Silver City, New Mexico is now a thriving downtown arts district. But don’t head to Main Street for the good stuff. In 1895, much of Main Street was washed out by floods, leaving little more than a 55-foot ditch that is now a leafy park. In order to cope with the damage, store owners simply opened their back doors, making parallel-running Bullard Street the new “Main Street.” Today, Bullard’s colorful buildings and Rococo brick cornices reflect Silver City’s artistic flair and reputation. On any given day, Mexican-style restaurants and art galleries showcasing local Southwestern-style art will be hopping with people, but the place really comes alive during festival season. Over the course of the year, downtown Silver City plays host to the Silver City Blues Festival, Red Paint Pow Wow Wow, the Tamal Fiesta y Mas, and Southwest Festival of the Written Word, among others.
29. Holland, Michigan
Holland, Michigan’s main street is West Eighth Street, a four-block stretch that ends near beautiful Lake Macatawa. The street is a vibrant locale with plenty of appealing restaurants and cafes, boutiques, bookstores, and galleries to step into and shop. Unique for the northern states, West Eighth Street is pedestrian friendly even in winter, thanks to a state-of-the-art snow melting system. Otherwise, follow the herd to Holland in the spring, when the town hosts their famous Tulip Time Festival in celebration of their Dutch heritage.
28. Healdsburg, California
Situated within the gently rolling hills of Sonoma County, Healdsburg, California is known for its agriculture, olive oil, and wineries. Like so many of the formerly Spanish towns near the Bay Area, Healdsburg’s “main street” is actually a central downtown plaza ringed with high-end boutiques selling everything from jewelry to local fashion, world-class restaurants, art galleries, independent bookstores, antique shops, and more. The plaza is especially busy at night, when visitors and locals gather for dinner and wine tasting after a day of hiking or biking the gorgeous local terrain.
27. McMinnville, Oregon
Tiny McMinnville, Oregon is located in the midst of Willamette Valley wine country, and the home of renowned local wineries like R. Stuart & Willamette Valley Vineyards, Terra Vina, Remy Wines, Woodard Wines, and Elizabeth Chambers Cellar, to name but a few. Downtown McMinnville is a charming haven of turn-of-the-century buildings that have been lovingly restored into wine bars and tasting rooms, art galleries, and chic boutiques. Stop in at one of the downtown farm-to-table restaurants, and you’ll understand why Bon Appetit magazine recently named McMinnville as one of America’s “foodiest towns.” Downtown also plays host to a number of beloved annual events, including the second largest UFO Festival each May, the highly respected International Pinot Noir Celebration held every July, and Turkey Rama, a summertime tradition going back more than 50 years.
26. Traverse City, Michigan
Situated on the edge of Grand Traverse Bay in northwestern Michigan, Traverse City is one of the most up-and-coming towns in the Midwest — and for good reason. The surrounding region is fondly known as the Cherry Capital of the World, an honor that is taken very seriously by downtown Traverse City. The main downtown street, Front Street, plays host to the annual National Cherry Festival, during which people travel from all over the United States to sample and buy everything from cherry salsa to cherry candles. The only local festival that comes close to the festivities of the Cherry Festival is the Traverse City Film Festival, created by local filmmaker Michael Moore. The heart of downtown is the Village at Grand Traverse Commons, which is one of the largest historic preservation and adaptive reuse projects in the world. Surrounding the Village are award-winning Italian restaurants, the popular Right Brain Brewery, and local winery tasting rooms like Left Foot Charley.
25. Lahaina, Hawaii
Visitors to Maui should check out the small town of Lahaina and its main Front Street. Briefly a capital for 1800s Hawaiian royalty, Front Street is now a cluster of two-story wooden buildings with wraparound balconies and porches. Here, tourists can catch a whale-watching tour, or shop for everything from coral necklaces and other art pieces to refreshing Hawaiian cocktails. At the end of the road, an enormous Banyan tree makes for a favorite photo op. Amidst the fun, Front Street also offers a sobering piece of history. The Wo Hing Museum, once a cultural center for Chinese plantation workers, and the restored Baldwin House, once the home of a missionary family, offer two views of what island life was like before it became a mecca for mainlanders.
24. Bath, Maine
Located on Kennebec River, it’s easy to see why Bath, Maine has become known as the “City of Ships.” Before the downtown main street, Front Street, ends at dry docks and shipping cranes, it’s a tree-lined pedestrian’s paradise full of historic brick buildings turned shops, restaurants, and bakeries. Highlights include Reny’s, a small discount department store that is a cool throwback to an earlier era. Also on Front Street is the Maine Maritime Museum, which offers an entertaining overview of Bath’s shipbuilding history from wood to steel.
23. Solvang, California
Little Solvang, California sits in the hills of Santa Barbara County. It was founded in 1911 by a group of Danes who had traveled west in hopes of establishing a Danish colony. Today, Solvang’s main street is a little slice of Denmark on America’s West Coast. Bakeries, restaurants, art galleries, and boutiques line both sides of the street, most of them with facades and architecture reflecting traditional Danish style. A 1:3 scale replica of Copenhagen’s Round Tower sits in the town center, and nearby are statues of Hans Christian Andersen and the Little Mermaid. Mission Santa Ines, one of the California missions listed as a National Historic Landmark, is also located nearby.
22. Columbus, Mississippi
Located on the Tombigbee River in northeastern Mississippi, Columbus is the birthplace of celebrated playwright Tennessee Williams. In fact, Williams’ old Victorian house is now the official welcome center on Main Street. Downtown Columbus has become more and more buzzworthy in recent years, and young locals have flocked to condos and apartments located directly above Main Street businesses and restaurants. Street level, the Hitching Lot Farmers’ Market run weekly from April to October, while live music, festivals, and contests like watermelon seed spitting and corn shucking, are popular during the summer months.
21. Ridgefield, Connecticut
Ridgefield, Connecticut’s downtown Main Street has been called a “Norman Rockwell painting come to life.” Indeed, the picture perfect street is bookended by a classic steepled church and a beautifully constructed library. Step inside the local hardware store and savor the creaky floorboards, or take in the more modern Ridgefield with a visit to Aldrich Contemporary Art Museum. Whatever your preference, don’t leave Ridgefield without stopping into Deborah Ann’s Sweet Shoppe for a taste of delicious homemade chocolate.
20. Red Lodge, Montana
Set against the backdrop of the Beartooth Mountains, Red Lodge’s main Broadway Avenue is part of the 80-mile Main Street to Mountains Rocky Fork Trail, used to access the wilderness just outside town limits. Broadway was once a stomping ground for such figures as Calamity Jane, Wild Bill Hickok, and the Sundance Kid, who once robbed a bank on Broadway. Today, the street is full of restored two-story buildings, many of which with their original Wild West facades, now housing shops, restaurants, and galleries. One such treasure is the 1893-built Pollard Hotel, where Buffalo Bill and Calamity Jane once stayed.
19. Wallace, Idaho
Wallace, Idaho is home to less than 1,000 people, but can boast one of the most enchanting downtowns in the western United States. It’s main drag, Bank Street, is a classic American main street, with the added bonus of having a stunning mountainscape backdrop. Bank Street’s elegant brick buildings, constructed in the Italianate style, originate from the days of Wallace’s silver boom. Visit any of Wallace’s restaurants, galleries, or shops for a pleasant afternoon, but to get a better idea of Wallace as a historically significant town, visit the Oasis Bordello Museum, which offers tours and a cheeky history of one of the five Wallace bordellos that once “served” the mining community.
18. Coeur d’Alene, Idaho
Coeur d’Alene, Idaho is a small town surrounded by 55 glacier-filled lakes and the Coeur d’Alene Mountains (the very tip of the Northern Rockies). The town’s main street, Sherman Avenue, was once called “a little slice of Heaven” by Barbara Walters. Indeed, it is a major destination for nature enthusiasts looking to enjoy a resort town. Located lakeside, Sherman Avenue is flush with art galleries, cafes and restaurants, and mom-and-pop shops. It’s the site of the yearly IRONMAN competition, as well as the annual Coeur d’Alene Holiday Light Show, which features over 1.5 million lights and one of the largest living Christmas trees in the world.
17. Walla Walla, Washington
Walla Walla, Washington’s downtown main street is a pedestrian paradise. More than a dozen local wineries operate tasting rooms downtown for visitors to enjoy between checking out the many public art installations, boutiques, antique stores, and the Walla Walla Symphony, the oldest continuously operating American symphony orchestra west of the Mississippi River. And visitors certainly won’t go hungry downtown. In fact, Walla Walla was called one of the country’s eight “Best Small Towns for Food,” and downtown samplings include such celebrated restaurants as Brasserie Four, Graze, and the Maple Counter Cafe. In recent years, Walla Walla has found its way onto a number of “best of” lists. Sunset Magazine called it one of the 24 “best places to live and work,” Fodor’s added it to its list of the ten “Best Small Towns in America,” and both Rand McNally and USA Today named it one of “America’s Friendliest Small Towns.”
16. DeLand, Florida
From the outside, DeLand, Florida may look like a sleepy southern town, but don’t let first impressions deceive you. The town’s downtown, and especially its main street of Woodland Boulevard, is an artistic and cultural hub. Art galleries, cafes, restaurants, bookstores, and boutiques are plenty and almost always lively, partly due to the close proximity of Stetson University (which also boasts a scenic campus). Those interested in doing more than shopping or eating should step into the Museum of Art, or stick around for any one of DeLand’s full calendar of festivals, parades, and special events.
15. Eureka Springs, Arkansas
Settled within the beautiful Ozarks, Eureka Springs, Arkansas is listed on the National Register of Historic Place — yep, the entire town. Downtown Eureka Springs oozes charm, and its main street is lined with trees and Victorian architecture. Don’t let the hilly terrain deter you; simply hop on the working trolley car to make your way around what was once a hotspot for those seeking the local curative hot springs. Today, people flock to downtown Eureka Springs for the art galleries, the darling Queen Anne-style B&Bs, and the eclectic music scene. Don’t leave town without visiting the Mud Street Cafe, or the E. Fay Jones-designed Thorncrown Chapel with its huge glass panels.
14. Hailey, Idaho
Located in the Wood River Valley, Hailey, Idaho boasts a large tourism industry. Most visitors flock to Hailey for the nearby ski resorts, hiking trails, and fishing holes, though the downtown area is nothing to sneeze at either. Trails connect the entire community to downtown’s Main Street, where restaurants, shopping, and entertainment options are plentiful. A rodeo ground and ice-skating rink are also located nearby. Head to Hailey’s downtown during the summer and catch the acclaimed Northern Rockies Music Festival.
13. Victoria, Texas
Downtown Victoria, Texas is chock full of interesting and significant historic architecture, a feature consistent with its reputation as the believed starting point of Texas history. Over the last few decades, massive preservation efforts have led to the restoration of more than a hundred properties now listed on the National Register of Historic Places. Visitors can take a guided tour through the downtown streets to view such gems as the Victoria County Courthouse, the Museum of the Coastal Bend, and the historic McNamara House turned social history museum. The most popular hangout downtown is easily the 562-acre Riverside Park, where visitors can take in the Texas Zoo, walk along the Victoria Paddling Trail, or take a relaxing boat ride on Lake Texana. Finally, downtown Victoria especially comes alive in October, when the Bootfest Festival comes to celebrate local music, culture, and cowboy boots.
12. Deadwood, South Dakota
Stepping into historic downtown Deadwood, South Dakota is like stepping back in time to the Wild West. The town of approximately 1,200 people has spent upwards of $300 million in order to restore the once infamous gold mining town — an effort that has been rewarded with the title of National Historic Landmark for the entirety of the city limits. Deadwood’s Main Street looks remarkably like it did in the 1800s, complete with gaming halls, restaurants, and hotels. The thousands of visitors who flock to downtown Deadwood every year enjoy shopping in any of the dozens of locally owned shops, and touring everything from historic homes, to the nearby Broken Boot Mine, to the graves of such Wild West legends as Calamity Jane and Wild Bill Hickok.
11. Collierville, Tennessee
Collierville, Tennessee’s main Town Square is truly the heart of the city, and combines the perfect mix of old Americana with modern economic success. The Square overlooks timeless favorites such as Collierville Depot, the old McGinnis Service Station, an antebellum log cabin, Gus’s World Famous Fried Chicken, and the Silver Caboose Restaurant. And visitors to Collierville aren’t recommended to leave until they’ve tried an old fashioned soda or ice cream from Mensi’s Dairy Bar. Every May, the Town Square hosts Fair on the Square to kick off a summertime of farmers markets and a free concert series. Finally, the Square backs up to Confederate Park, a turn-of-the-century park full of charming walkways, cast-iron fences, and even a traditional American bandstand. Sound charming? It is. Parade Magazine recently named Collierville’s Town Square “America’s Best Main Street.”
10. Mackinac Island, Michigan
Stepping onto Mackinac Island feels like stepping back in time to America’s Golden Age. Virtually one road exists on the island, the main part of which is located adjacent to the shuttle boat dock. Cars are banned, so bicycles and horse carriages pass charming bed and breakfasts, traditional taverns, old fashioned fudge and candy shops, chic boutiques, and so much more. Bookending the cobblestoned main street are the 1700s fort and the world famous Grand Hotel, which overlooks the famous Tea Garden and Esther Williams swimming pool. If you can’t visit Mackinac in person, you can see the charming street and landscapes in the classic film “A Moment in Time.”
9. Saratoga Springs, New York
Since Saratoga Race Course first opened in 1863, Saratoga Springs has been a chic and sophisticated getaway for New York horse racing fans. The town itself boasts more than twenty golf courses, mineral springs, bathhouses, and tranquility spas. After a long day on the golf course or at the race track, most weekend Saratogans flock to downtown Broadway Avenue. Adjacent to the race course, Broadway is home to a number of Beaux Arts and Colonial Revival-style buildings housing museums, dance halls, boutiques, restaurants, and art galleries. Charming sidewalk cafes offer tables and benches beside overflowing flowerbeds, but the largest crowds will flock to Caffe Lena, the oldest continuously operated coffeehouse in America where such names as Bob Dylan, Arlo Guthrie, and Don McLean once played.
8. Bardstown, Kentucky
First settled in 1780, Bardstown, Kentucky is a charming small town listed on the National Register of Historic Places. Bardstown’s Main Street is located directly in the center of its acclaimed Historic District. Buildings from the 18th and 19th centuries line the road on both side, the most interesting of which include the Nelson County Jail, Old L & N Station, and the Old Talbott Tavern — all of which appear individually on the National Register as well. Most of the street’s architecture is Federal or Georgian in style, making it an absurdly picturesque location for a leisurely stroll. Stop by Main Street after visiting the Jim Beam or Makers Mark bourbon distilleries just down the road, and wander into Bardstown’s charming boutiques, antique shops, and restaurants.
7. Nantucket, Massachusetts
All 105 miles of charming Nantucket, Massachusetts are listed on the National Historic Register, but the heart of the town is undoubtedly cobblestone-lined Main Street. Lined with Greek Revival buildings, elm trees, and benches, Main Street is the perfect paradise for a stroll amongst galleries, boutiques, cafes, and so much more, all with old-fashioned storefronts. In the summer, visitors can take a break from people watching to pick up everything from needlepoint belts and anchor-shaped door knockers, to the classic and handmade toys. Continue walking and eventually you’ll end up at the busy harbor, once the whaling capital of the world. Finally, end your day on Nantucket’s Main Street with a visit to Nantucket Pharmacy, an old-fashioned soda counter still serving delicious scoops and old style milkshakes.
6. Hot Springs, Arkansas
Often referred to as the first resort town in America, Hot Springs, Arkansas is now home to — you guessed it — some of the purest hot springs in the world. In fact, the town is actually part of a National Park, and includes eight historic bathhouses which draw water straight from the springs without any special treatment. Hot Springs’ downtown is the aptly named Bathhouse Row. A stroll along the Row will take you past Quapaw, Buckstaff, and other turn-of-the-century bathhouses built in Neoclassical and Renaissance Revival architectural styles. Also located on Bathhouse Row are plenty of antique stores and art galleries, as well as the Arlington Hotel, where guests can request to stay in the room once frequented by Al Capone. End a day on Bathhouse Row at Superior Bathhouse Brewery & Distillery, the only brewery in the area that is permitted to use water from the springs.
5. Staunton, Virginia
The hometown of President Woodrow Wilson, little Staunton is located in Virginia’s beautiful Shenandoah Valley. Downtown, Staunton’s Beverley Street was the first in the state to win the National Trust for Historic Preservation’s Great American Main Street Award. The street is lined with brick buildings. In fact, Staunton has the highest concentrations of late 19th century architecture in the United States. Gems amongst this treasure of a main street include the Blackfriar’s Playhouse, a recreation of Shakespeare’s London theater, and the Camera Heritage Museum, which tells the story of photography with more than 2,000 cameras.
4. Virginia City, Nevada
Virginia City, Nevada is a 150-year old former mining town isolated in the Sierra Nevada Mountains. Once a gold rush boomtown and the place where Mark Twain began his writing career, Virginia City is now a fully restored Wild West Town full of historical reenactments, dressed-up characters, theaters and opera houses, and preserved facades and buildings. In between shopping the boutiques and tourist traps (why mine gold when you can buy it?), stop in at such famous hotspots as the Bucket of Blood Saloon, the Old Washoe Club, or the Comstock Fireman’s Museum. If nearby hiking, camping, cycling or horse-back riding adventures aren’t enough to keep you busy, there are also countless historic homes and restaurants that have been lovingly restored for the enjoyment of visiting history buffs.
3. Galena, Illinois
Located amongst rolling hills Galena, Illinois is famous as the hometown of famous Civil War general and 18th U.S. President Ulysses S. Grant. More than 1,000 Galena buildings have found a place on the National Register of Historic Places, many of which are located downtown. Indeed, taking a stroll along Main Street is like stepping back in time. The DeSoto House Hotel, which has served locals and tourists alike since 1855, hosts a trivia quiz night each year on President Grant’s birthday. Horse-drawn trolleys pass colorful buildings housing restaurants, old fashioned chocolate shops, galleries, boutiques, and more. Street festivals are common throughout the year, while wine tastings and downtown ghost tours are available daily.
2. Paso Robles, California
Paso Robles, California is beautiful countryside located between Los Angeles and San Francisco. Though the town was originally founded around natural hot springs, today it is best known for the 200 wineries that grace the nearby hills. Downtown, Paso Robles boasts a main square lined with gorgeous buildings ranging from high Victorian to Mexican adobe style. The square offers visitors everything from a movie theater, to restaurants of all kinds, to rotating exhibits, to chic boutiques, to wine tastings, and much more. Visitors to Paso Robles can also catch a wine tour from the main square, on which they can learn all about the Pinot Noirs and Zinfandels that hail from the region.
1. Fort Pierce, Florida
Fort Pierce, Florida’s downtown Main Street is easy to spot — its lined with palm trees, a pedestrian sidewalk, benches for resting, and unique Spanish Colonial architecture. Shopping opportunities are plenty, though the old Arcade Building, Boston House, and the A.E. Backus Gallery & Museum are also worth checking out. Better yet, hop on a boat tour of the Indian River Lagoon and Swampland and spot dolphins, manatees, any number of bird species, turtles, and flora. The Saturday morning Farmers Market brings out quite the crowd, as does the monthly Friday Fest. Other Main Street festivals throughout the year include March’s Taste of the Sea & Sandy Shoes Seafood Festival, and the Sights & Sounds Christmas festival and parade held each December. Main Street is also the recipient of the 2011 Great American Main Street Award by the National Trust for Historic Preservation for its effort in preserving the 1923 Sunrise Theater, which was badly harmed during a 2004 hurricane.