America’s Best Main Streets

Friendly neighbors, family-run businesses, and quaint restaurants serving comforting diner fare—these are the images conjured up by the phrase “Main Street USA.” Even in this fast-paced era, many small towns have held onto their historic roots and preserved their central thoroughfares. From a harbor town on the west coast with ornate Victorian architecture, to Key West’s colorful Duval Street, visitors can find unique cultural attractions and warm, welcoming communities in small towns across the country. A few steps along each of these main streets prove that small-town America is alive and well—and can hold its own against larger, neighboring cities. Here are our picks for America’s best main streets.

By Emily Wasserman

WHERE: Galena, Illinois

Galena’s Main Street epitomizes small town America. Just three hours outside Chicago, Galena provides a retreat from urban hustle and bustle. The downtown area includes antique shops, restaurants, and boutiques—all housed in mid-19th century storefronts. Visitors can browse the work of local artists at the street’s art galleries or stop by the DeSoto House Hotel for a breakfast or lunch buffet. Those with a sweet tooth will enjoy Galena’s old-fashioned ice cream parlor. Guests can choose from more than 40 flavors of ice cream and sample old-fashioned sodas, floats, malts, and shakes.

PLAN YOUR TRIP: Visit Fodor’s Galena Guide

WHERE: Port Townsend, Washington

Once named the “City of Dreams,” Port Townsend was slated to become the West Coast’s largest harbor. Plans changed—but the town still retains much of its original charm. Visit Water Street to explore historic business districts and watch Victorian ships sail across the water. Port Townsend Gallery showcases the work of some of the town’s best artists, and visitors can sample house-made ales at Port Townsend Brewing Co. Stop by The Spice & Tea Exchange for gourmet seasonings and spices as well as custom-made rubs and blends.

PLAN YOUR TRIP: Visit Fodor’s Port Townsend Guide

WHERE: Denton, Texas

Just north of Dallas, Denton boasts a vibrant community with attractions for every age. Main Street is located next to the city’s historic courthouse and features unique shops, numerous dining options, and a variety of museums, galleries, and art venues. Watch live performances outside the courthouse, or browse one of the street’s antique stores. A Creative Art Studio features the work of local artist and offers classes for budding artists. For a sweet treat, visit Denton Square Donuts: the store is open during evening hours so you can satisfy your late night cravings.

PLAN YOUR TRIP: Visit Fodor's Texas Guide

WHERE: Woodstock, Vermont

This picturesque Vermont town belongs on the back of a postcard. Tree-lined streets, pristine homes, and quaint shops make Woodstock an ideal travel destination. The town’s Center Street features rustic brick buildings and ends at a park overlooking a picturesque river bridge. Get your hands dirty at Billings Farm & Museum. Guests can learn how to milk a cow or participate in a butter-making workshop.  Stop by the artist owned and operated Collective- The Art of Craft, to browse the work of local artists. End the day at The Lincoln Inn’s Mangowood restaurant, which offers fresh, seasonal fare with a creative twist.

PLAN YOUR TRIP: Visit Fodor’s Woodstock Guide

WHERE: Charleston, South Carolina

Step back in time on Charleston’s Broad Street. The city oozes Southern charm and its famous Historic District features sprawling mansions, horse-drawn carriages, and palm tree-lined paths. The street is divided into North and South regions, each with their own distinct character. Visit North of Broad for shopping and delicious eateries, or travel south for oak-shaded parks and picturesque private homes. Take a tour of the Nathaniel Russell House for an up-close look at ornate, 19th-century architecture. City Market, on the street’s north side, features open-air stalls with handmade crafts, produce, and regional souvenirs.

PLAN YOUR TRIP: Visit Fodor’s Charleston Guide

WHERE: Saratoga Springs, New York

Also known as the “Queen of Spas,” Saratoga Springs was named for its abundant mineral waters. Now a popular horseracing destination, the town features a historic main street with colonial-style buildings, boutiques, and benches perfect for people watching. Stop by the Saratoga Farmer’s Market for fresh, local produce, poultry, and baked goods, or head to the Saratoga Racecourse to watch thoroughbreds compete for the top title. For authentic Saratoga-style barbeque, look no further than PJ’s; the 50s style drive-in is located on the city’s main street, and visitors can enjoy tender ribs and brisket at outdoor picnic tables.

PLAN YOUR TRIP:  Visit Fodor’s Saratoga Springs Guide

WHERE: Bath, Maine

Located on the Kennebec River, Bath is best known for its maritime culture and 19th-century architecture. Historic mansions and homes line the city’s Front and Centre Streets, and visitors can take a walking tour of some of the area’s main attractions. Browse regional artwork at the Centre Street Arts Gallery, or enjoy music from local artists at the Chocolate Church Arts Center. Visit Front Street to explore quaint antique shops and bookstores, or stop by Centre Street’s natural market for a taste of fresh produce.

PLAN YOUR TRIP: Visit Fodor’s Bath Guide

WHERE: Eureka Springs, Arkansas

Fun is the name of the game in Eureka Springs. The vibrant Southern town features colorful nightlife, charming Victorian buildings, and a variety of dining options. Take a trolley through South Main Street for easy access to shops and restaurants then end the night at a welcoming B&B. Locals and tourists love Local Flavor Café, an eclectic eatery with fresh, creative cuisine. Dance the night away at Eureka Paradise, one of the city’s most popular nightclubs, or enjoy live music and pub fare at Chelsea’s Corner Café. 

WHERE: Littleton, New Hampshire

With a stunning mountain backdrop and picturesque river, it’s easy to see why Littleton remains New Hampshire’s commercial hub. The town’s Main Street boasts historic buildings, specialty shops, and a number of cultural attractions. Climb the cupola at Thayers Inn for 360-degree views of downtown, or browse old photos in the inn’s lobby and halls. Adults and children will enjoy Chutters, a sweets shop that boasts the world’s longest candy counter. To experience the town's industrial history, visit Schilling Beer Co. on nearby Mill Street for handcrafted European-style lagers and ales. The brewery is housed in a renovated 18th-century mill building, and it cooks rustic artisanal fare on a wood-fired oven from its taproom, which overlooks the Ammonoosuc River.

PLAN YOUR TRIP: Visit Fodor’s Littleton Guide

WHERE: Paducah, Kentucky

Located between the Ohio and Tennessee Rivers, Paducah offers a rich history and a variety of cultural attractions. The town’s LowerTown Arts District is home to a number of eclectic antique shops and galleries, while the historic downtown area features specialty markets, restaurants, and museums. Browse Paducah artifacts at the William Clark Market House Museum, or stop by Stornoway House Gallery for an up-close look at local art. Movie lovers will enjoy Maiden Alley Cinema, the town’s fine film venue.

PLAN YOUR TRIP: Visit Fodor's Kentucky Guide

WHERE: Richmond, Indiana

Visitors will be swept away by Richmond’s winding, tree-lined roads, red brick houses, and quaint Victorian architecture. The town features ornate churches and farm homes and offers a number of cultural attractions and museums. Take a walking tour of the area’s buildings, most of which house family-owned businesses and shops. You’ll feel as if you’ve stepped back in time at Main Street Diner, an old-fashioned eatery that serves reasonably priced fare. 

WHERE: Staunton, Virginia

Don’t let Staunton’s small size fool you. The Virginia town boasts over 100 quaint shops, art galleries, and restaurants and has made a name for itself as a premiere arts and cultural destination. Beverley Street, the town’s main thoroughfare, is lined with museums, specialty stores, and eateries, and is best explored by foot. For Southern-inspired cuisine in a contemporary setting, visit Zynodoa.  Photography lovers will enjoy the Camera Heritage Museum, which features more than 2,000 specialty cameras and lenses. Staunton was also the birthplace of Woodrow Wilson, and the town’s Woodrow Wilson Presidential Museum and Library pays homage to the 28th president.

PLAN YOUR TRIP: Visit Fodor’s Staunton Guide

WHERE: Ann Arbor, Michigan

A quintessential college town, Ann Arbor, and its South Main Street reflect a vibrant culture. The city offers something for visitors of all ages, from hands-on museums with interactive exhibits, to colorful bars and restaurants. Enjoy acoustic music at The Ark, a nonprofit venue that features performances from renowned folk performers. Choosing just one of South Main Street’s restaurants might seem like a herculean task, but a good option is The Ravens Club. The kitchen and bar offers seasonal farm-to-table cuisine and a cocktail menu with an impressive collection of whiskey. 

PLAN YOUR TRIP: Visit Fodor's Michigan Guide

WHERE: San Luis Obispo, California

Sandwiched between Los Angeles and San Francisco, San Luis Obispo often gets lost in the shuffle. But the city boasts a rich history dating back to the 19th century and a lively downtown area. The main thoroughfare, Higuera Street, features quaint indoor plazas that border a rippling creek, and nearby Mission San Luis Obispo de Tolosa hosts some of the town’s most popular festivals. Don’t miss the Farmers’ Market held weekly on Thursday night and Saturday morning. Visitors can browse stands selling flowers, vegetables, and produce, and snack on crepes, pizza, or barbeque while enjoying live music.

PLAN YOUR TRIP: Visit Fodor’s San Luis Obispo Guide

WHERE: Key West, Florida

Few places compare to Key West, and the island’s Duval Street provides plenty of local color. Although sprawling Victorian mansions line the southern end of the thoroughfare, most attention is given to the northern end of the street. Every night, locals and tourists make their way to the gulf shores for the “Duval Pub Crawl,” a tour-de-force of the area’s most popular restaurants and bars. It isn’t unusual to see costumed patrons singing and dancing in the street, and the carnival-like atmosphere continues into the wee hours of the morning.   

PLAN YOUR TRIP: Visit Fodor’s Key West Guide