9 Northern United States Towns With Unforgettable Main Streets
Far from a cookie-cutter city plan, a charming, vibrant Main Street area can make for an unforgettable getaway. Experience Groundhog Day with small-town delights, try the Cherry Capital of the World, visit a museum dedicated to Katharine Hepburn, or experience Bavaria without ever leaving the country. Take a walk to restaurants offering the best of local delights, shop with small businesses and local artisans, and experience town squares and wide, walkable historic streets that continue to offer an exceptional quality of life to residents and new favorite spots for visitors.
Traverse City, Michigan
Visit Front Street in Traverse City to find outfits for outdoor adventures, local art, vintage finds, books, and much more. Try Embrace the Cherry Capital of the World with a stop at Cherry Republic for everything cherry under the sun, including wine, salsa, shortbread cookies, and barbecue sauce. Shop small and vintage at Slip Vintage, where you can even book a denim fitting. Visiting in the fall? Front Street is the site of the annual Downtown Traverse City Halloween Walk, where costumes are encouraged and candy is plentiful. Nearby, the Old Town Playhouse is ideal for a night on the town, with a full mainstage season of volunteer-driven shows.
Ashland, Wisconsin
Ashland features an eight-block Main Street Business District, which is listed on the National Register of Historic Places, and it is a haven for public art. The area is known as the Historic Mural Capital of Wisconsin, so a self-guided mural walk is a must. Seasonal trolley tours are also available. The beautiful downtown architecture is worth a stroll, but take the time to pop in at the locally owned shops like Home Expressions for one-of-a-kind gifts and souvenirs. When you’re ready to take a break, try Gabriele's German Cookies & Chocolates for German pretzels, homemade truffles, and other treats.
Bennington, Vermont
Billed as Vermont’s oldest town, Bennington has plenty to see, including the world’s largest collection of Grandma Moses folk art and Vermont’s oldest Protestant church. A self-guided walking tour is a great place to start exploring downtown. (The town offers a driving option as well.) See the historic, freestanding clock on Main Street that was installed in 1929, and then visit the Bennington Museum, which got its start in 1852. In addition to folk art, the museum features history, temporary exhibits reflecting Vermont, and even a Cabinet of Curiosities that lets visitors create their own stories about a wide variety of items on display.
Spencer, Iowa
Spencer’s Main Street district is a thriving scene where arts, dining, and shopping all come together for a full day of exploring. Spencer Community Theatre is in its 65th year of performing, with main stage shows and a children’s theatre program. For a very special souvenir, Vermeer Glass Art Studio & Gallery features vibrant glass art pieces. And for a break and a chance to visit with locals, The Iowa Project Brewing Company is the spot for a pint, and if you time your visit well, maybe a round of trivia.
Leavenworth, Washington
Experience a bit of Bavaria in Leavenworth, with a postcard-perfect backdrop of Alpine architecture, German food, and much more. The town is surrounded by the Cascade Mountains, enhancing the already breathtaking views. Of course, there’s gingerbread (try The Gingerbread Factory for decorated and undecorated houses, as well as traditional Lebkuchen heart cookies) and plenty of spots for beer and sausages. Festival season is rich with tradition. Oktoberfest features music, a street fair, and activities for all ages, and the downtown even has a Winter Karneval that brings January to life.
Hood River, Oregon
Downtown Hood River’s Historic District has been revitalized for a new era, while maintaining its charm. Nestled among evergreens and mountain views, shopping and dining on and around Oak Street is enough to fill any visitor’s itinerary. Start the day with breakfast from Doppio Coffee and Lounge before heading to the 301 Gallery to shop with local artists. The gallery is located in the historic Butler Bank building, which also features an apartment available for nightly or monthly rentals. Look for artist receptions on the First Friday of each month from April through December. For a custom gift, visit Apland Design for one-of-a-kind jewelry.
Chadron, Nebraska
Start a visit to Chadron with a visit to the Chadron Chamber of Commerce and Visitors Bureau for information about a self-guided tour of the city’s downtown district, which is on the National Register of Historic Places. Don’t miss Main Street’s Art Alley, home to a growing list of murals that enliven spaces at every turn. The local art project has expanded beyond Main Street, bringing color and community to the area. Eat like a local on Main Street with breakfast at Just Love Coffee and Café and dinner at The Ridge.
Woodstock, Illinois
Woodstock Square in the city’s downtown was featured in the movie “Groundhog Day,” and its charm is enough to make visitors want to come back again and again. Visit the farmers' market and shop for unique finds like used books at Carpetbagger Books or handcrafted tea blends at Casting Whimsy Tea. Take a break in the square and have a meal at Corner Square Café. On Sunday afternoons in the summer, look for Sunday Art in the Square, where you can shop directly from local artists. Planning a winter visit? January and February bring Groundhog Day, because in this town, the celebration lasts more than one day.
Old Saybrook, Connecticut
With a hefty dose of seaside magic, historic Old Saybrook has all the laid-back charm visitors could want, with plenty to see and do. Make the first stop a visit to the Greater Old Saybrook Chamber at 1 Main Street, for details and guides to all the town has to offer. Catch a show at The Katharine Hepburn Cultural Arts Center. Known as “The Kate,” it opened in 1911 and is listed on the National Register of Historic Places. More than a theater, The Kate also serves as a museum honoring its namesake, who was a resident of Old Saybrook. Visitors can find breakfast and lunch at the Paperback Café, but save room for dinner at Liv’s Oyster Bar, which has a menu that is heavy on locally sourced goods.
Whether you are looking for a cooler take on summer, vibrant fall color, winter adventures, or a festival overflowing with nostalgia, a journey north can offer a chance to see historic sites and experience downtowns bursting with charm. These spots boast beautiful Main Street areas where visitors can shop, dine, and live like a local, even if it is just for a weekend getaway. Plan to stroll, taste, and escape to a place you won’t soon forget.
