These eight cities have the quaintest, cutest, most walkable streets in the country.
Walking down a town’s main street and browsing the collection of local shops, or stepping into restaurants and feeling a strong sense of community is a special way to appreciate a destination. These downtown main street roadways across the U.S. offer visitors and locals alike the opportunity to experience what might just be the cutest, most picturesque roadways to roam. These main street thoroughfares were practically purposefully designed to enjoy a leisurely stroll.
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Park City, Utah
The Historic Main Street in Park City, Utah, comprises 47 landmark buildings listed on the National Register of Historic Places. Among them, there are roughly 100 independent boutiques, 50 delectable restaurants, and a wide variety of fine art galleries and historical museums to explore. As there’s an “anti-chain” business rule, visitors can always count on enjoying an authentic Main Street strolling experience that can only be found in Park City. Step into the array of local saloons and live music venues—including the only ski-in/ski-out distillery in North America–High West Distillery. Snow sports enthusiasts can even take advantage of chair lift access by traveling directly to historic Main Street through Park City Mountain Resort. Surrounded by stunning mountain sights any time of year, whether it’s changing leaves or powdery snow, Park City’s quaint Main Street always feels like a journey back in time to another era.
Georgetown, District of Columbia
Georgetown, D.C., with its striking, federal-style architecture, picturesque Potomac River, and quaint, walkable cobblestone streets make for a charming historic district to experience. The neighborhood’s Main Street corridor offers endless opportunities to step into some of the tastiest restaurants in the region and explore dozens of stores ranging from small boutiques to well-known retailers. Grab a treat from the legendary Georgetown Cupcake, where there’s always a spirited line outside the door. Those who are feeling fancy should check out Cafe Milano, which is a known hot spot for politicians and celebrities seeking an elegant night out. Sip on a cocktail at CUT Above at the Rosewood Washington, D.C.—a rooftop bar with gorgeous birdseye views of the capital’s majestic skyline. Extend the visit with a night at the opulent The Ritz-Carlton, Georgetown, Washington, D.C., offering a quiet, intimate hotel experience set within a beautifully restored historic industrial building.
Just an hour’s drive northwest of San Antonio is Fredericksburg—an authentic Texas-German community with a welcoming spirit, and historic heritage. Fredericksburg’s Main Street is the center of the action in the town, with more than 150 shops, boutiques, art galleries, restaurants, wine-tasting rooms, and even a couple of museums. And as part of Fredericksburg’s National Historic District, Main Street is free of franchises. Grab a keepsake from the Fredericksburg General Store along Main Street’s “Magic Mile” of shopping. Stop into Fischer & Wieser on Main, a locally-owned family business with humble origins as a roadside peach stand—today, serving samples of their highly regarded, gourmet products. Art enthusiasts can’t miss Insight Gallery and Gallery 330, both of which feature an impressive array of artists. Wine lovers can sip and savor at Narrow Path Winery and Becker Vineyards on Main after enjoying a bistro and gourmet market at Vaudeville.
In the 1800s, gold was discovered in what’s today known as the town of Breckenridge, Colorado, and prospectors flocked to this new mining destination in search of fortune. Today, travelers are still drawn to Breckenridge’s hearty spirit and timeless charm—there’s always something to do on Main Street Breckenridge with its incredible shopping and dining scene, serving as the central hub for hosting fun events, festivals, music, and an abundance of activities year-round. Grab a bite at Crepes A La Cart where there’s nearly always a line, and enjoy a sweet or savory crepe. Further down the street, upscale eatery Rootstalk is an ideal stop for a romantic date night, serving curated cocktails and seasonal specialties. Mountain View Coffee Bar is a top-notch spot to grab a morning brew with a view—and Broken Compass Brewery’s Main Street taproom is perfect for enjoying an evening brew.
When many people think of “Tennessee,” they immediately think of Nashville—but just outside of this big city, travelers can explore the relaxing destination of Franklin, which boasts a beautiful 16-block historic district that’s even listed on the National Register of Historic Places. The area is anchored by a scenic town square and encompassed by charming Victorian architecture with a vibrant Main Street boasting more than just a storied history. Explore the range of unique shops, dining outposts, antique boutiques, and more. And within the boundaries of Franklin, visitors will also find the quaint village of Leiper’s Fork—a known spot for famous artists and musicians to escape the crowds and enjoy some peace. This charming neighborhood boasts a small but mighty Main Street and downtown area home to a collection of lovely inns, restaurants, antique shops, and art galleries made for leisurely exploring.
The Main Street of Jackson, Wyoming, is a quaint, walkable street boasting a plethora of businesses and restaurants—almost all of which are independently owned and operated. Eat at Persephone’s bakery which is just a few steps off the main drag, for breakfast or lunch. This French-inspired bakery is known for its freshly baked artisanal breads and homemade pastries created from ingredients sourced from local farms in and around Jackson Hole. Stop into the Million Dollar Cowboy Bar or Silver Dollar Bar to enjoy a drink at an iconic town staple watering hole. Visit the Jackson Hole Historical Society and Museum to learn about the rich history of this Wild Western town. Finally, stop to take photos under one of the four antler arches that grace the Town Square. Spend the night at The Wort Hotel—the oldest hotel in Jackson—to experience a bit of history and relaxation.
Lake Geneva, Wisconsin
Lake Geneva, Wisconsin, which sits between the big cities of Chicago and Milwaukee, emits the energy that travelers are seeking from a classic lake destination and resort town getaway, blending small-town charm with upscale lodging, amenities, and dining opportunities. Main Street is the heart of this local community and features a range of quaint boutiques, eateries, confectioneries, and art galleries. Grab a beer at Topsy Turvy Brewery, which occupies a historic former church. Sample locally made cheese at Hill Valley Dairy, or grab a craft cocktail at Maxwell Mansion speakeasy – Apothecary Bar. Experience more of downtown’s culinary offerings at stops like Avant Cycle Cafe—a full-service bicycle and coffee shop—or locally owned and operated business, The Farm Stand, which serves sandwiches, soups, and salads alongside market goods like fresh honey, cheese curds, organic eggs, and more, with an open patio for relaxing.
Nestled into the heart of peaceful Amish country, Lititz, Pennsylvania’s Main Street is dripping in charm, boasting businesses housed in traditional American architecture. Visitors can stroll throughout downtown’s classic buildings which today are home to forward-thinking businesses. Grab a coffee at Slate Cafe, which sells pastry creations like the Northeast classic—whoopie pies, and even homemade dog treats for furry family members. Visit A Tea Affair for a beautiful selection of teas and scones. Stop into The Lititz Shirt Factory just off the main drag, which has been lovingly restored and transformed from an old factory into a hip live music venue and brewery. And steps away, the iconic Wilbur Chocolate Factory has become a world-class luxury hotel called “The Wilbur Lititz” which still celebrates its “sweet heritage.” But in homage to its origins, it’s common to hear the clickety-clacking of horse hooves pulling Amish carriages through this storied town.