40 of the Best Main Streets in America You Need to Visit ASAP
Plan your next trip around these quaint, idyllic strips.
Whether you're a city slicker or rural native at heart, it's near impossible for anyone to resist the undeniable charm of a quaint small town, be it the handful of mom-and-pop businesses that you can't find anywhere else or the completely idyllic scenery.
What many of these provincial paradises lack in size and population, they more than make up for in their quintessentially old-school main streets, some spanning several blocks in the heart of each mini metropolis. Lucky for you, we've rounded up some of the best small-town main streets in the U.S., each boasting picturesque ice cream shops, eateries, antique stores, bed and breakfasts, and even special annual events.
Plan your next family getaway to any of these homey locales across the country—from Colorado to North Carolina and everywhere in between—because once you take a look at these cozy spots, you'll want to add them all to your travel bucket list ASAP.
Beverley Street in Staunton, Virginia
We're more than a little jealous of folks who live in Staunton year-round. As visitors, we love diving into a cup of gelato at The Split Banana, grabbing a coffee or beer and hanging in the garden at The By & By, and treasure hunting at Made: By The People. Come nightfall, Beverley Street hums with energy, thanks to spots like farm-to-table restaurant Zynodoa and Yelping Dog Wine Bar.
Main Street in Galena, Illinois
Wake up each morning in an 1850s-mansion-turned-B&B: Abbey's High Street Bed and Breakfast. Then, spend your day picking up fresh produce from the Galena Farmers Market, which takes place every Saturday from May to October. Stop by one of the many antique shops before sitting down to a homemade pasta dinner from locally owned Vinny Vanucchi's "Little Italy."
Derby Street in Salem, Massachusetts
Salem's downtown district has charm at every turn, but on Derby Street, you'll find this adorable flower shop, David Engs Flowers, and the aptly named Witch's Brew Cafe.
Thames Street in Fells Point, Maryland
Take a break from the hustle and bustle of Baltimore and visit Fells Point, one of the city's oldest neighborhoods. Arrive in style on a water taxi, which is a great way to see the area, and shuck some fresh oysters at Thames Street Oyster House (which hosts a popular happy hour Monday through Friday).
Main Street in Callicoon, New York
Settled by the Dutch in the 1600s, this art-imitates-life Main Street reads more country western than east coast (especially with the 1852 inn-and-supper club, the Western Hotel). As you wander through vintage shops and pass by old train tracks, mighty mountains infuse your view with vivid greens in one of Sullivan Catskills' finest undiscovered gems.
Mission Drive in Solvang, California
Founded by Danish immigrants, who first settled the area in the early 1900s, Solvang looks like something out of a fairy-tale—complete with a windmill. But Mission Drive will be just the start of your adventure. The surrounding Santa Ynez Valley is packed with vineyards, making this the perfect homebase if you love a fine beverage. Before you leave town, be sure to visit the "Little Mermaid" statue—it's an exact replica of the one in Copenhagen, but half the size.
Main Street in Bar Harbor, Maine
Located on Maine's Mount Desert Island, Bar Harbor boasts both swoon-worthy mansions and sweeping manors—some of which you can stay in (like the beautiful Bar Harbor Inn). But its Main Street is its own visual delight. That's thanks to the colorful clapboard buildings that line the street, all the way down to the undeniably romantic waterfront. As it's the state's official fruit, the town takes special pride in whipping up the best blueberry desserts, so don't skip a taste.
White Mountain Highway in North Conway Village, New Hampshire
Once upon a time, you dropped us off at Zeb's General Store, and with its spectacular collection of New England specialty food, we decided we never wanted to leave. When you finally pry us away, we're moseying on over to Schouler Park and Conway Scenic Railroad, a fantastic old-timey station. Once you're done taking in the quintessentially New England white-steepled church and mountain scenery, sling back the fun at White Mountain Winery, where you select your favorite vino and create a custom label.
Washington Street in Cape May, New Jersey
Cape May may be famous for its many colorful Victorian gingerbread homes—but its main street, Washington Street, is just as delightful. You'll find upscale boutiques (Victorious and Queen May) alongside a classic five-and-dime—which, yes, boasts a Grease-worthy soda fountain (Margie D's Soda Fountain at Dellas 5&10). And, of course, there's plenty of fine dining, including the adorable Louisa's Cafe, a pint-sized haven for seafood lovers.
Downtown Mall in Charlottesville, Virginia
Get your day started on Charlottesville's eight-block row lined with restaurants, shops, and mighty oak trees—in a region that several of our Founding Fathers have called home (Thomas Jefferson, James Monroe, and James Madison). The architecture of the buildings found along the Downtown Mall is charming with a distinct Southern and historic feel. For tantalizing eats, try Brasserie Saison and The Fitzroy.
Central Street in Woodstock, Vermont
Whether you visit in the fall for peak foliage season or during the holidays when Central Street is lined with Christmas trees and twinkly lights, Woodstock is always worth the trip. The Yankee Bookshop is irresistibly charming—and you'll never regret a stay at Woodstock Inn & Resort.
Ocean Avenue in Carmel-by-the-Sea, California
This city is famous for its small, but beautiful, beach, the historic Carmel Mission, and, of course, the many fairy-tale cottages that line its main street, Ocean Avenue. With its picturesque setting, it is perhaps no surprise that there are more than 100 galleries within its limits. Pop into the Sunset Cultural Center for everything from rock concerts to stand-up shows, and venture outside the village for vineyards galore, including KORi Wines and De Tierra Vineyards.
Main Street in Vail, Colorado
Tucked within the White River National Forest, Vail is a prime spot for winter activities, including skiing and snowboarding. But if you're not so into sporting, there's an equally appealing option: Vail Village, a pedestrian-friendly area designed to look like old-world Bavaria. The shopping options, however, are very much of today (we're talking art galleries, fine jewelers, luxe après ski boutiques, and, yes, a Patagonia). As for food, you can never go wrong with the longtime modern American favorite, Sweet Basil. Don't forget your summer options! Once the snow melts, Vail offers hiking, biking, and plenty of entertainment at the The Gerald R. Ford Amphitheater (a.k.a. "The Amp"), including the annual concert and BBQ series, Moe’s Original BBQ Hot Summer Nights, as well as the Vail Dance Festival.
M Street in Georgetown, Washington, D.C.
One word to describe Georgetown's M Street? Gorgeous. The historic downtown, which actually encompasses both M Street and Wisconsin Avenue, is filled to the brim with boutiques, both unique, multi-brand shops (like Lili the First) and mass favorites (like Madewell). As for where to eat, we suggest turning onto Wisconsin and turning into Lutèce, the reboot of the Georgetown classic, Cafe Bonaparte. You can go a la carte or opt for the chef's tasting menu—which, at $95 a person, isn't cheap—but then, can you really put a price on a great French meal?
Cookman Avenue in Asbury Park, New Jersey
If you're a Springsteen diehard, you'll need to stop by The Stone Pony, where he first made his name. But you should also explore Cookman Avenue, Asbury's well-stocked main street, which includes the adorably named Homesick (the main restaurant) and Lovesick (the adjoining wine bar pictured here). Once your stomach's full, walk Cookman all the way down and you'll eventually hit the boardwalk, the highlight of which is still the Asbury Park Convention Center, a living ode to 1920s seaside architecture.
Main Street in North Myrtle Beach, South Carolina
No trip to North Myrtle Beach would be complete without wandering Main Street and reliving that childhood vacation high on this nostalgia-imbued strip. Of course, there's also the adult version of fun: grabbing a blanket and holing up where road melds into sand and enjoying live music in the ban shell for Music on Main. The next day, you'll likely need some hair of the dog at Coconuts Tiki Bar and Grill and a burger from Pirate's Cove. Or, you know, a restorative dip in the ocean.
Main Street in Eastsound on Orcas Island, Washington
A modern-day Mayberry indeed. We're loving this coastal town's tree-studded Main Street that's brimming with boutiques, galleries, and eateries perched over Fishing Bay. You're going to want to swing by Emmanuel's Labyrinth to steal a moment of blissful solitude and lush views. For historic digs, check into Outlook Inn, which has been operating for over 100 years.
Old Salem's Main Street in Winston-Salem, North Carolina
Bring comfortable shoes, ladies and gents. And for sustenance, grab a bite at Winkler Bakery, where Moravian sugar cake, bread, and cookies still come to life in a 200-year-old, wood-fired oven.
Main Street in Ogunquit, Maine
When we're not relaxing at the nearby Cliff House resort, we're strolling Ogunquit's ever-charming Main Street. Grab a morning coffee from Mornings in Paris—and later, right off of Main Street, on Shore Road, stop for a scoop or two from Sweet Pea's Ice Cream before you hit the nearby waterfront.
Main Street in Park City, Utah
Summer Sundays are practically made for the Park Silly Sunday Market, where live music, craft artisans, and delicious food vendors abound. Loaded Bloody Mary in hand, explore the festival by foot on historic Main Street for a day that will linger in your memories fondly for years to come. If you're not in town for the market, the strip still bleeds with mountain-town charm. Grab some grub on the year-round heated rooftop patio at No Name Saloon and then navigate your way through art galleries, cafés, and boutiques. Shouting distance from Main Street is the famed Washington School House that still feels secluded from the bustling downtown, thanks to its spectacular mountain views.
Perri is a New York City-born and -based writer; she holds a bachelor’s in psychology from Columbia University and is also a culinary school graduate of the plant-based Natural Gourmet Institute, which is now the Natural Gourmet Center at the Institute of Culinary Education. Her work has appeared in the New York Post, Men's Journal, Rolling Stone, Oprah Daily, Insider.com, Architectural Digest, Southern Living, and more. She's probably seen Dave Matthews Band in your hometown, and she'll never turn down a bloody mary. Learn more at VeganWhenSober.com.
Rose Marie Walano is a freelance editor and children's author. (And a Cosmo alum!) Among the many things she loves are high tea, period dramas, Central Park, K-pop, and her adorable mini-doodle, Colette. You can follow her on Instagram at @rosiewalano.
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