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Whether you're a city slicker or a rural native at heart, it's nearly impossible to resist the undeniable charm of a quaint small town, be it the handful of mom-and-pop businesses you can't find anywhere else or the 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 an adorable flower shop, David Engs Flowers, and the aptly named Wolf Next Door coffee shop.
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 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.
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). 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.
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). 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 along the Downtown Mall is charming, with a distinctly Southern 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 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 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.
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 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?
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 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.
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. 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, 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.
Main Street in Nantucket, Massachusetts
While the whole of Nantucket is historic, there's something about Main Street's quaint cobblestone, Greek Revival mansions and soaring church spires that make you feel like you've stepped back in time. The Daffodil Festival is one of the town's multiple seasonal events, but perhaps the most charming, as both the streets and the cars—many of which are vintage—are decorated in the sunshine-hued flower.
Main Street in Southampton, New York
Spotted: A main street worthy of Gossip Girl. While each of the Hamptons has its own chic high street, Southampton's Main Street is particularly adored for its boutique shopping. Between high-end name brands, like AERIN and Ralph Lauren, you'll find one-of-a-kind bookstores, jewelry stores, cheese shops, and the Tate's cookies flagship (reason alone to visit, we say!).
East Main Street in Beacon, New York
Just about a one-hour train ride north of New York City, snug on the Hudson River, is Beacon, an emerging hub for the contemporary arts. Dia: Beacon makes the best case for that—if you're a modern art lover, it's a must. For the nature-minded, Beacon offers Breakneck Ridge, a gorgeous trail that overlooks the Hudson. But it's Beacon's downtown, filled with galleries, great food (The Vault and Sukhothai are our top picks), and a beautiful waterfall, that makes Beacon for absolutely anyone.
Colorado Avenue in Telluride, Colorado
As locals know, there's seriously no bad views in Telluride. And as you stand upon this sprawling thoroughfare that hangs below the Rocky Mountains' imposing peaks and wide-open sky, it's hard to disagree. In the winter, enjoy seeing skiers walk along this road to nearby lifts. In the summer, block parties abound, with hits including a July 4th parade and a New Orleans-style Second Line Parade for the Telluride Jazz Festival. Get to know some of the 2,595 warm and hospitable locals, and you'll see why this is a small town with a big reputation.
Main Street in Breckenridge, Colorado
Not too far from Vail, you'll find another Colorado town with European vibes: Breckenridge. Its historic downtown area sets it apart, as it's preserved from the days when prospectors first came hunting for gold (circa 1859). Outside the city, there are all-season activities galore, from dog sledding in the winter to hiking in the summer (the Reiling Dredge trail starts close to town).
Main Street in New Iberia, Louisiana
Marvel at the art-deco Evangeline Theater (now the Silman Theater, this spot is now on the National Register of Historic Places) before finding your way to Shadows-on-the-Teche, a striking historic house. In the core of Cajun Country, you'll find the fresh air and stunning views as revitalizing as the welcoming locals.
Jackson Hole Town Square in Jackson, Wyoming
While, yes, a park, Jackson Hole's Town Square has all the charm of a main street. It has local artisans and a toy shop, but it's perhaps most famous for its iconic four arches, each of which is made out of elk antlers. The first arch was erected in 1953, and it was such a hit with tourists, the others followed shortly thereafter. Although, none of the arches are original, because elk antlers do not last forever!
Main Street in Mystic, Connecticut
You've, of course, heard of Mystic Pizza, the setting of Julia Roberts' 1988 film of the same name. (Tagline: "A Slice of Heaven!") But that's just the start of what you can find in this seaside village. There's the Mystic Seaport, a recreated, 19th-century seafaring village, and the Mystic Aquarium, where you'll find fish, whales, and dolphins. And then there's Main Street itself—so classic, it boasts a metal shop (Danforth Pewter) and a fudge shop (Kenzie's).
Main Street in Harwich Port on Cape Cod
Ah, there's nothing quite like the welcoming breeze and laid-back vibe of Cape Cod. Here, you can hit up all the mom-and-pop shops you want, get a scoop of some of the best ice cream in the country, and slurp up some stellar clam chowder at beloved staple, The Mad Minnow. Port Summer Nights on summer Wednesdays run through Labor Day and pulse with the energy of live music, lively vendors, stellar food, and that unmistakable strain of summertime magic on the Cape.
Market Street in Frederick, Maryland
There's more to this impressive avenue than Top Chef contestant Bryan Voltaggio's restaurant, The Ordinary Hen. On Market Street, you'll find everything from Pretzel & Pizza Creations to The North Market Pop Shop, which features 400 kinds of vintage soda that can be paired with locally made ice cream for an unforgettable float. Bonus: Market Street connects to Carroll Creek Park, a linear park reminiscent of San Antonio's famed Riverwalk.
Main Street in Dahlonega, Georgia
You know a city's not joking around with its Main Street when it wins the 2016 award for Great American Main Street City from the National Trust for Historic Preservation. Between all the good shopping and eating, catch a show at the beautifully restored Holly Theater. Southern Appalachian charm chimes palpably here too, with cool events throughout the year, like the Gold Rush Days Festivals and the Southeast's largest bicycle event, Six Gap/Three Gap.
Main Street in Carmel, Indiana
Midwestern loveliness beams brightly here, in an area known as the Arts & Design District. Pose with the life-sized statues (there are 17 in total, ranging from a violinist to a policeman) for some fun photo ops and hop into Silver in the City for some quirky jewelry. Next up, chow down at Woody's, a library-turned-restaurant, and liquor up at Peace Water Winery, a tasting room that gives away half its profits to charity.
Main Street in Ellicott City, Maryland
After recovering from a massive flood, Ellicott City has rebounded and rebuilt their Main Street, reaching vibrant new heights. Running parallel to the Tiber River and cutting straight through the historic district, it's hard to decide where to start. But here's one thing you can't miss: The loot at Sweet Elizabeth Jane, a local vintage-inspired lifestyle store named for the owner's grandmother.
Main Street in Greenville, South Carolina
Embrace childhood glee at Mast General Store, where the penny candy barrels certainly strike a chord with our heart. Or, get your crunch on at Poppington's, where the Bloody Mary and dill popcorn are both unreal.
Main Street in Aspen, Colorado
Aspen may have big-city culture, but its old-timey Main Street exudes all the charms of country Western days of old. The Aspen Music Festival is an eight-week festival with more than 800 classical music students in town, teachers from Juilliard and other institutions, and some of the most renowned classical musicians in the world. There are more than 300 events during the festival, from opera to chamber to full orchestral to master classes.
Main Street in Rockland, Maine
Some of the perks of visiting this quaint street include Atlantic Baking Co. and lobster at Claws, which has a fun deck scene that overlooks Rockland Harbor. No trip to Rockland would be complete without a visit to The Strand Theatre for a film, live music, or performance. And before your Main Street adventures conclude, a cold one at Rock Harbor Brewing is a must, especially at night when the pub typically has trivia, open mics, cribbage tournaments, or live music.
Broadway in Saratoga Springs, New York
After a dip in a rejuvenating mineral bath at Roosevelt Bath and Spa, your energy will be through the roof for scoping out this upbeat boulevard. Grab a pick-me-up at BARE Blends Saratoga before poking around Northshire Bookstore, an indie book shop with lots of stellar gifts. Even if you're not hungry—yet—grab a Tallulah to-go at Putnam Market and bike 20 or so minutes to Saratoga Spa State Park. There, you can plop down at a picnic table beside an awe-inspiring spring and read the afternoon away. Ready to call it a day? Retreat to the Geyser Lodge Bed and Breakfast, conveniently located within walking distance of both the town and the park.
Main Street in McCarthy, Alaska
Small-town main streets don't get much better than this remote, former Alaskan mining town. Enjoy the allure of McCarthy at the picturesque Ma Johnson's Historic Hotel and The McCarthy Lodge. Wake up restored and ready to tackle a day, stumbling into mom-and-pop shops on this central drag or exploring Wrangell-St. Elias National Park and Preserve, which the town is contained within. Once you're done hiking for the day, try The Potato for a celebratory beer and well-deserved garlic curly fries.
Main Street in Annapolis, Maryland
Annapolis is, of course, home to the U.S. Naval Academy. But it's also home to a historic district with an extremely cute downtown area. Walk down Main Street—filled with restaurants, bars, art galleries, and a bookstore—and you'll find architecture that spans four centuries. The best part is that the Annapolis Harbor serves as its stunning backdrop. We recommend taking it in as the sun sets, with a cone from the Annapolis Ice Cream Co. in hand.
Main Street in Eureka Springs, Arkansas
Nestled in the Ozark Mountains, Eureka Springs instantly transports you to another time when Victorian buildings were the norm and a relaxing vacation included a dip in a natural hot spring. While the perfectly preserved architecture on Main Street is a big draw, we can't have you go without also visiting the Thorncrown Chapel, E. Fay Jones's incredible modern chapel in the woods, featuring more than 6,000 square feet of glass. It's free to enter and breathtaking to behold.
