These Are the 41 Most Gorgeous Main Streets Across America

Salem's downtown district has charm at every turn, but on Derby Street, you'll find an adorable flower shop, David Engs Flowers, and the aptly named Wolf Next Door coffee shop.

Situated off an expansive green, West Street in historic and quaint Litchfield, Connecticut, is the epitome of small-town New England. Start with a coffee and croissant from The Bakehouse, then browse the clothing, home, and antique stores lining the street, including House Beautiful Best Home Stores winner Milton Market. Finish the evening with cocktails or dinner at The Abner or Belden House, two top-tier hotels within walking distance.

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.

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.

Founded by Danish immigrants who first settled the area in the early 1900s, Solvang looks like something out of a fairytale, 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 home base if you love a fine beverage. Before you leave town, be sure to visit the "Little Mermaid" statue—it's a replica of the one in Copenhagen, but half the size.

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). Its Main Street is a visual delight, thanks to the colorful clapboard buildings lining 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.

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.

Cape May may be famous for its many colorful Victorian gingerbread homes, but its main street, Washington Street, is just as delightful. There, 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). Of course, there's plenty of fine dining, including the adorable Louisa's Cafe, a pint-sized haven for seafood lovers.

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 along the Downtown Mall is charming, with a distinctly Southern feel. For tantalizing eats, try Brasserie Saison and The Fitzroy.

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.

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 De Tierra Vineyards.

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 sports, there's an equally appealing option: Vail Village, a pedestrian-friendly area designed to look like old-world Bavaria. Once the snow melts, Vail also offers hiking, biking, and plenty of entertainment at 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.

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 and mass favorites. As for where to eat, we suggest turning onto Wisconsin and ducking into Lutèce, the reboot of the Georgetown classic, Café Bonaparte. You can go à 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?

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 Brickwall (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.

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 the road meets the sand and enjoying live music in the band 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.

We're loving this coastal town's tree-studded Main Street 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.

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.

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 Main Street, stop for a scoop or two from Sweet Pea's Ice Cream before you hit the nearby waterfront.