Whoever said that bigger is better never set foot in these postcard-perfect small towns. If you’ve ever caught a bluegrass concert in Black Mountain, polished off a lobster roll in Ogunquit or climbed aboard a scenic train tour in Jim Thorpe, you know that sometimes, less really is more.
This small town vacation roundup only features destinations less than 20 square miles in area, because we believe good things come in small packages—and when it comes to historic sites, outdoor adventures and genuinely great people, each one of these places packs a big punch.
Whether you’re looking for somewhere to go sailing, skydiving or gallery-hopping, we’re making it easy to find a charming small town to explore the next time you’re ready to hit the road. Better yet? We’re also making it easy to find and book an affordable place to stay before you arrive. Choosing a vacation rental over a hotel means extra living space, a full kitchen and even outdoor spaces like a porch or patio area with a BBQ grill.
And once you decide on a destination, you can book all your tours, activities, and attractions right on TripAdvisor, too. Our new 24-hour cancellation policy (on experiences) means you can pre-book before arriving, but still have the flexibility to cancel if your itinerary changes.
Click through the slideshow below to discover gems across the country, from Camden and Cooperstown on the East Coast to Avalon and Port Angeles out West. And congrats to our readers’ choice winner Black Mountain, North Carolina for being voted the prettiest small town vacation in America.
You don’t need to spend much time in downtown Aspen to understand why the popular destination has such a glamorous reputation. From the chic, high-end boutiques and restaurants to cultural hotspots like the Wheeler Opera House and the Aspen Art Museum, this small town is more than the sum of its famously challenging slopes. If you’re here to ski, don’t forget to reserve all your gear.
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Thirty miles off the coast of Los Angeles, Avalon—a gorgeous small town on Catalina Island—lures travelers with seaside views, hilltop cafes and first-rate water sports from scuba diving and snorkeling to sailing and kayaking. If sunbathing is more your style, book a villa near the beach, claim a chaise lounge and settle in for a lazy afternoon snooze. There are plenty of top-quality tours to book: try this three-hour walking and food tour of the island, this glass-bottomed boat trip to see leopard sharks, moray eels and more, or go all out and see the island from the sky on a helicopter ride
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This Oregon Coast destination is a scenic spot for golf, fishing and horseback riding—not to mention exploring. Make time to visit the charming Old Town district and historic lighthouse. One reviewer writes, “We walked to the Coquille River Lighthouse on the way to our vacation rental. It was nearly dusk, so we enjoyed the beautiful reds and oranges of the sunset.”
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If you like to be pampered, then a trip to Berkeley Springs—the country’s original spa retreat—is definitely in order. Relax and de-stress in the historic mineral spring baths at Berkeley Springs State Park, or splurge on a massage at one of the full-service spas nearby. Don’t leave without treating yourself to a taste of this small town's famous apple butter.
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Visit Black Mountain, and you’ll want to sit down and stay awhile. From summer to fall, rocking chairs painted by local artists appear outside downtown shops (a nod to the spot’s nickname, “The Little Town that Rocks.”) Dotted with locally-owned restaurants and art galleries, this gem in the Blue Ridge Mountains is full of nostalgic charm—thanks in part to local landmarks like the Town Hardware & General Store.
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Home to one of the best-known ski resorts in the country, Breckenridge boasts more than 2,300 skiable acres and an irresistible downtown district featuring rows of restaurants and boutiques. One reviewer writes, “We rented a house one block off Main Street in a beautiful, walkable area. The view of the mountains was breathtaking.”
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Maine is full of small coastal towns, but Camden must rank among the most charming. Reviewers describe it as “picturesque” and “a pure delight,” and from the historic homes to the scenic location on Penobscot Bay, it’s not hard to see why. Make the most of those bay views on a daytime or sunset Windjammer sail.
Maybe it’s the friendly community, striking scenery or convenient lake access. Maybe it’s the art galleries and shops in the center of town, or the bike trails that begin here and trace a path to cities beyond. Whatever it is about Charlevoix that lures you in, there’s no question that this small town on the coast of Northern Michigan deserves a spot on your list of places to visit.
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When it comes to “the Great American pastime,” Cooperstown is undoubtedly home plate. You might know this one-stoplight town thanks to the National Baseball Hall of Fame, but it also draws fans of The Last of the Mohicans author James Fenimore Cooper, who spent much of his childhood there. Prepare to be smitten with the quaint Main Street shops and glimpses of the Adirondacks and Catskills in the distance.
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Today, the site of America's first major gold rush is better known for its wine country location than its valuable ore. In addition to having the highest concentration of wineries, vineyards and tasting rooms in the state, Dahlonega is also home to art galleries, boutiques and museums. And did we mention that the Chattahoochee National Forest is right next door? (That's what we like to call an embarrassment of riches.) What’s more, if there are ghosthunters in your party, they can get to grips with the city in spine-chilling style on a historic ghost walk.
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Fernandina Beach has all the makings of a quintessential American beach town: it’s clean, pretty and family-friendly, with a rich history and a wide variety of outdoor activities. Located on the north end of Amelia Island, this delightful destination boasts Victorian-era architecture and hospitable locals—just in case you needed two more reasons to book a rental and pack your bags.
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Looking for a small town to visit near the Windy City? Galena, surrounded by green hills and family farms, is perched in the state’s scenic northwest corner. The real draw here is Main Street, a six-block district known for its variety of architectural styles. Explore the boutiques and galleries downtown before hopping on a trolley tour or admiring the original furnishings at the Ulysses S. Grant Home State Historic Site.
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Once dotted with cattle ranches and dairy farms, Heber City’s history peeks out in the area’s rolling fields and artisan cheese. Catch a ride on the Heber Valley Railroad or head out to hike, bike or ski; with so many mountain peaks and streams nearby, this small town has fast become a year-round hub for nature lovers and outdoor enthusiasts.
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This small town in the Missouri River Valley dates back to 1837. With more than 110 buildings on the National Register of Historic Places, Hermann has developed a reputation for its 19th-century architecture and proud German heritage. Whether you visit for the antique shops and flea market finds, the Hermann Wine Trail or the Katy Trail—the longest rails-to-trails project in the nation—this is a memorable getaway spot.
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Whether you’re a foodie, thrill-seeker, history buff or true outdoor enthusiast, Hood River is the kind of once-in-a-lifetime getaway you need on your bucket list. The showstopper here is undoubtedly the beautiful Columbia River Gorge, which you can discover by guided boat tour. One reviewer writes, “Take your time. Stop often. Smell the sage during springtime. Check out the windsurfers and kiteboarders navigating the Columbia River. Take a winery tour or do a dessert dash in this adorable town filled with folks who know good ingredients. There's something here for everyone—and you'll want to come back.”
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Jim Thorpe ranks high on our list of small country towns to visit thanks to its walkable downtown, historic sites and awesome outdoor attractions (think mountain biking, cross-country skiing and whitewater rafting). Best of all, its central location—80 miles from Philadelphia, 120 miles from New York City and 200 miles from DC—makes it a convenient weekend getaway for city dwellers up and down the Mid-Atlantic.
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This coastal community plays host to a packed calendar of exciting events, from an annual independent film festival to an award-winning weekly farmers market. Lewes entices travelers with a storied nautical heritage and a downtown district known for its 17th-century architecture and quaint little shops.
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Moab is home to some of the country’s most popular national parks and jaw-dropping natural landscapes, so it’s no surprise that thrill-seekers flock here for rock climbing, skydiving, mountain biking, canyoneering, extreme whitewater rafting, and off-roading adventures. Whether you want to free fall thousands of feet or hike through Arches National Park, you’re in for a one-of-a-kind combination of big adventures and small-town hospitality.
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It’s no coincidence that “America’s First Resort” is often heralded among the country’s best small towns. From quiet coastal trails and vintage oyster shacks to Gilded Age mansions and fine dining in Bowen’s Wharf, this idyllic seaside spot in Narragansett Bay offers a sophisticated take on the New England beach town experience. Get out and explore those grand residences on a dedicated trolley tour.
This bustling resort town on Maine’s southern coast has a lot to offer, beginning with 3.5 miles of beaches and Marginal Way, a seaside trail that traces the rocky shoreline. Once known as a popular artists’ colony, Ogunquit boasts a vibrant cultural scene that includes a playhouse and an American art museum.
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If you want to experience Maui in a low-key setting full of friendly locals (including Willie Nelson), then there’s a good chance you’ll adore this under-the-radar spot on the North Shore. One reviewer writes, “Paia is a bohemian surfer town with lots of organic restaurants, independent shops and uncrowded beaches. We love it here! Our rental host even left us a bottle of wine and tropical flowers that made the entire house smell heavenly.” Get some incredible views when you book an action-packed biking or ziplining adventure.
Can’t decide between the mountains and the ocean? Make a break for Port Angeles, a scenic port sandwiched between the Strait of Juan de Fuca and Olympic National Park. In the heart of downtown, you’ll discover cafes, galleries, antique shops and independent bookstores; you can even take a guided walking tour of the historic underground business district.
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Once a Victorian seaport, Port Townsend is surrounded almost entirely by water, which makes it the perfect setting for regattas, races and boat festivals of all kinds. Go gallery-hopping in the downtown historic district, book a whale watching tour or curl up with a good book in one of the cute local coffee bars.
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Even as St. Augustine has risen in popularity, it hasn’t lost its small-town charm. With historic landmarks like Ponce de Leon’s Fountain of Youth and cobblestone streets shaded by ancient oaks, this centuries-old city will steal your heart—history buff or not. Explore it on a trolley tour or helicopter trip.
Take one look at its red-rock vistas and striking pine forests, and you’ll understand why Sedona served as the setting for dozens of classic Westerns. Located 100 miles south of the Grand Canyon, it’s a hotspot for posh spas, art galleries and natural scenery—including 1.8 million acres of national forest land. Rent a home to escape the downtown crowds and explore the spectacular rock formation. There are loads of exciting tours to help you explore this fascinating terrain—book ahead to grab your place.
The largest island in Georgia’s Golden Isles offers up coastal charm in a pristine setting. Once home to rice and cotton plantations, St. Simons Island boasts beautiful, under-developed beaches—perfect for bodysurfing at high tide and biking along the sand when the waves pull away. With its moss-draped oak trees, winding roads and mild weather, this small town is an idyllic destination year-round. Why not take in the tastes and history of this place on a guided walking tour?
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Located on Florida’s Treasure Coast, the self-proclaimed “Sailfish Capital of the World” should rank high on your list of small coastal towns to visit for its natural beauty and colorful local history. One reviewer writes, “Stuart is old and new Florida at its best. This is the perfect place to spend a sunny afternoon; you will definitely want to stop for ice cream or homemade fudge at one of the quaint local shops.”
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You might know Woods Hole for ferry service to Martha’s Vineyard, but the historic Cape Cod village isn’t just a place to pass through. With its deep-water harbors, family-friendly beaches and iconic marine science institutions, this gem by the sea is a destination in its own right.
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Update: voting is closed as of December 19, 2016. Congratulations to Black Mountain, North Carolina for winning our readers’ choice prettiest small town vacation in America! The artsy outdoor paradise edged out second-place finisher Stuart, Florida and third-place finisher Jim Thorpe, Pennsylvania to take the crown.