Is there anything more appealing than a small town with a cute main street? They almost beg you to walk a little slower, smile at everyone you pass, and spend the day wandering in and out of local shops and businesses. It almost feels like stepping back in time or into a Hallmark movie. Luckily, such places still exist, even in our modern era. Whether you’re looking for a weekend getaway or a quick day trip, small towns offer a chance to escape the noise of the city and truly relax. To help you plan your next small-town getaway, we went to the experts for their picks for the small towns with the cutest main streets.
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The Best Main Streets in Small-Town America
1. Custer, South Dakota
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Custer looks as if it was ripped from the screen of an old-time western movie. Founded as a gold mining town in 1875, Custer is the oldest community in South Dakota’s legendary Black Hills. Today, Custer’s main street is lined with historic buildings and businesses including the Gold Pan Saloon, a local watering hole dating back to the town’s beginnings.
"Custer, South Dakota has exploded in recent years as a place that visitors and locals alike want to be," says Katlyn Svendsen of the South Dakota Department of Tourism. "On the edge of Custer State Park and the Black Hills National Forest, this mountain town is a playground for nature seekers and is bustling with some of the hottest restaurants in the state. Downtown you’ll find art, vibrant restaurants, locally owned shops, and a charm that speaks to what once was and what could be again."
Along with being the gateway to Custer State Park, Custer is also a short drive from Mount Rushmore and the awe-inspiring Crazy Horse Memorial.
2. Fish Creek, Wisconsin
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The tiny town of Fish Creek is located on Wisconsin's scenic Door County Peninsula. Often referred to as the Cape Cod of the midwest, the county is adored for being home to many picturesque small towns on the shores of Lake Michigan including Fish Creek.
"The main street in the historic waterfront village of Fish Creek along Door County’s west coast takes folks back to a bygone era as they stroll down bustling streets of shops and restaurants in this Lake Michigan resort town," says Jon Jarosh of Destination Door County. It's got a plethora of unique shops, and galleries full of paintings, sculptures, and pottery crafted by local artists.
3. Oxford, Mississippi
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Oxford Mississippi has a rich history dating back to 1837, and period architecture helps bolster its claim to being home to one of the cutest main streets in the U.S.
"Oxford, Mississippi has been touted as the ‘Cultural Mecca of the South,’ evidenced by multiple James Beard Award-winning chefs, unique shopping, and a vivacious atmosphere that can only be found in ‘America’s Best College Town,’" says Kinney Ferris, executive director of Visit Oxford. "The historic Square, located in the heart of the destination, is our gathering place, offering visitors and locals alike an authentic Oxford experience as they walk around it, browsing art galleries, boutiques, restaurants, and bookshops."
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4. Sylva, North Carolina
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Nick Breedlove, Executive Director of the Jackson County Tourism Development Authority says Sylva, North Carolina is home to one of the cutest main streets in the U.S. "From the fall foliage and charming bookstores (including a rare finds bookstore) to antique stores and eclectic restaurants, Sylva’s Main Street is idyllic," he says. "Downtown is anchored on one end by the historic Jackson County Courthouse, and I always recommend visitors take the 107 steps to the top for stunning views of the Blue Ridge Mountains–it is the most photographed courthouse for good reason!"
Breedlove also says be sure to have a meal at ILDA, the artisan passion project of husband and wife team, Michelin-trained chef Santiago Guzzetti and sommelier Crystal Pace, when visiting downtown Sylva.
5. Yountville, California
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Napa Valley is known for being home to picture-perfect small towns set among the rolling vineyards and farms that make it one of the best wine destinations in the world.
"Yountville is truly the most stunning town in Napa Valley, with a one-of-a-kind charm that resonates throughout the entire community," says Luke Magnini, managing director of the luxury downtown hotel The Estate Yountville. "Its enchanting tree-covered walkways, outdoor sculptures, and slow-paced living make it the perfect choice for a Wine County escape.”
Downtown Yountville’s main street is home to 15 tasting rooms along with incredible shops, galleries, and restaurants.
6. Rehoboth Beach, Delaware
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Eric Ruth with the Delaware Tourism Office says Rehoboth Beach has one of the cutest main streets in the country. The town is also famous for its diversity.
"Rehoboth Avenue is a street that’s a little bit quirky: always very friendly, and ready to offer something for everyone, from families to LGBTQ travelers," says Ruth. "It’s the kind of place where the sheer breadth of experiences can be pleasantly startling—one minute you’re enjoying an ice cream cone as you watch the waves come in, the next you’re spending the evening at a drag bingo show or eating caviar.”
7. Colonial Williamsburg, Virginia
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"Colonial Williamsburg in Virginia has an especially charming main street named Duke of Gloucester Street, lined with historic buildings like taverns, a bakery, courthouse, and apothecary," Steve Prohaska, a travel expert with See The Best Places. "Visiting early in the morning before the tourist crowds arrive feels like being transported back to 18th-century America, where you'll be greeted by convincing actors in period costumes and hear the clop-clop of horse-drawn carriages on the cobblestone street."
He suggests popping into R. Charlton's Coffeehouse to sample hot chocolate or freshly baked cookies in a historic bakery. "Later in the day, you'll have the chance to watch and listen to a fife and drum performance."
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8. Eureka Springs, Arkansas
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Larry Snider, VP of Operations of Casago Vacation Rentals, is wild about Eureka Springs, Arkansas.
"This town is set in the Ozark Mountains and is known for its winding streets that cater to the hilly terrain," says Snider. "The entire town is on the National Register of Historic Places and is filled with adorable shopping and restaurants.”
Snider also shares this fun fact: There are no traffic lights in Eureka Springs since no two streets cross perpendicularly. In addition to being home to a cute main street, the area is also a haven for people seeking opportunities for outdoor recreation like camping, fishing, and mountain biking.
9. Natchez, Mississippi
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Natchez, Mississippi is one of the best towns in the South to explore on foot. The pedestrian-friendly downtown owes its roots to Natchez’s historic main street, offering an overwhelming array of shops such as ArtsNatchez and Darby’s, eateries including Pearl Street Pasta and Biscuits and Blues, museums, and historic home tours.
Nearby Bluff Park offers majestic vistas of the Mississippi River and brilliant sunsets in the evening. "We love sharing the unique atmosphere of Natchez," says Jessica Cauthen of Visit Natchez. "Our downtown is diverse and abundant with architectural beauty and vibrant culture, and a spirit that is optimistic, curious, and adventurous."
10. Ouray, Colorado
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This high alpine, 7,800 feet elevation Rocky Mountain town, originally settled during the Gold Rush era, has only 920 residents, but attracts hikers, ice climbers, and other outdoor enthusiasts from all over the country. Because of its spectacular setting surrounded by steep mountains on three and a half sides, Ouray is nicknamed the "Switzerland of America." Though it's not just the scenery that gives it a European feel and draws people in: The main street is listed on the National Register of Historic Places and offers plenty of things for visitors to see, do, and eat.
"As you walk down the charming street, certain buildings will make you feel like you're in Europe, while others will remind you of something out of the Old West," says Steven Geist, the travel writer behind Bro On The Go. "On many of the Western-style buildings, you will find plaques commemorating John Wayne because several scenes for his classic film True Grit were filmed here."
The biggest attraction for visitors along this adorable street is the Ouray Hot Springs Pool. "These geothermal heated mineral pools are open year-round," says Geist. "Visitors can relax in the sulfur-free waters while enjoying 360 views of the stunning San Juan Mountains."
Locals love the Ouray Brewery on Main Street, which not only has great beer, but delicious food and a rooftop with more of those gorgeous views. "Across the street, Outlaw serves premium cuts of steak in a cozy environment," says Geist. "This saloon-style establishment is said to have been Wayne's favorite restaurant in town."
11. Littleton, New Hampshire
New England Wanderlust
Nestled in New Hampshire's White Mountains, the town of Littleton is home to a main street that is straight out of a postcard, with an eclectic twist. Bookended by two white steepled churches, the street has scenic river views, but you'll also find awesome street art while strolling around, says Samantha Hamilton, the creator and writer of New England Wanderlust.
"The main street in Littleton is home to the longest candy counter in the world at Chutters, lovely independently-owned boutiques, amazing restaurants, a famous diner, and a historic inn where Ulysses S. Grant and Jimmy Carter once stayed," says Hamilton. "The next street over is Mill Street, which has the picturesque Schilling Beer Co. tap room and tasting room, and the beautiful Riverwalk Covered Bridge."
