Although the soft beauty of a mirror-like lake can leave you spellbound, the same for the terrifying grandeur of a rugged mountaintop, no words can accurately describe the experience of wandering through a beautiful town square drenched in charm and the restful rhythm of everyday life. It could be the nostalgic appeal around the stretch, the air of a bygone era, historic storefronts with beautiful flower planters, mind-rousing Victorian architecture, or narrow streets lined with moss-draped live oaks. While you should not judge a book by its cover, any location with an eye-catching town square belies aesthetic sensibility. Fortunately, the Northern United States has a good bunch of them. For specific recommendations, the following are the ten most charming town squares in the Northern United States.
Oskaloosa, Iowa
Downtown Oskaloosa, Iowa. Image credit: Paul Sableman via Flickr.com.
Oskaloosa is a small Iowa jewel and a colourful college town associated with William Penn University, named for the Quaker leader who founded Pennsylvania. With a historic bandstand smack in the middle of town, and right in the centrally located Oskaloosa City Square Park, an instant illustration of pure Americana, this town square deserves a spot among the most charming. Townsfolk often mill around the greens in the summer for events like Art on the Square, an integral part of Oskaloosa’s cultural landscape for a while. The same holds for the Annual Lighted Christmas Parade in the holiday season. Across the City Square Park is Smokey Row Coffee, a chill space with an impressive ice cream selection and lovely staff. Don’t forget to check out the indie bookstore next door (Book Vault), an unforgettable architectural gem that still has vaults from its previous life as a bank.
Jackson, Wyoming
Ski slopes in Jackson, Wyoming. Image credit: WitGorski / Shutterstock.com
Jackson is an underrated western Wyoming town that serves as the jumping-off point to several big names in the outdoor scene, including Grand Teton and the phenomenal Yellowstone National Parks. The town square, formally named George Washington Memorial Park, is a gorgeous space with corner arches made from elk antlers collected from the nearby Elk Refuge. Each arch is disassembled and recreated periodically. The space is drenched in an atmosphere of the American West, especially with all the enjoyable carriage rides and Old West shootout reenactments. Just off into the distance, there’s nothing but awe-inspiring mountains and beautiful open spaces. The Jackson Hole Historical Society & Museum offers walking tours of Jackson during the summer months. In the winter, the space comes alive with an ice-skating rink and lighted arches. Liberty Burger is a laid-back outpost that serves decadent artisanal treats, while MADE offers a mind-rousing selection of unique souvenirs and local artist offerings. Mursell’s Sweet Shop, right next door, is a cool spot to pass by for some flavorful homemade fudge.
Woodstock, Illinois
Street view in Woodstock, Illinois. Editorial credit: Nejdet Duzen / Shutterstock.com
Woodstock serves as a charming blend of history, culture, and electrifying events, including the fun-filled Groundhog Day celebrations, where fans get the rare chance to relive the iconic scenes from the 1993 classic movie Groundhog Day. Take note that Woodstock is proudly listed on the National Register of Historic Places and named a Distinctive Destination by the National Trust for Historic Preservation. Not just that. This overlooked Illinois gem has been designated as a Preserve America Community by the White House. Woodstock’s Historic Square, with its stunning 19th-century Victorian architecture, is certainly among the most delightful in the nation. The best part is that almost every corner here holds something special, whether musical instruments, fine art, antiques, exquisite jewelry, or eclectic dining options.
Amid the lush trees and bucolic atmosphere is the iconic Woodstock Opera House, whose history dates back to the 1880s. You can start with delicious prime ribs at the aptly named Squire on the Square, then check if there’s a show at the Classic Cinemas Woodstock XQ, loved for its reclining seats and impressive sound and picture quality. Also, you can crouch next to the water at the Dufield Pond Conservation Area and spend time with frogs and tadpoles.
Bar Harbor, Maine
The historic Main Street in Bar Harbor, Maine. Editorial credit: Sean Xu / Shutterstock.com.
With its idyllic green space, Bar Harbor is an incredibly dreamy spot that features everything you’d want from a public square. From a historic town clock to plentiful benches to a whimsical gazebo, Bar Harbor is among a few towns in the United States that are intentional about their aesthetic appeal. It even has a bronze fountain for making wishes. There’s the charm-soaked Village Green, which serves as a starting point for a day trip into the nearby Acadia National Park.
You can turn back the wheels of time at the Abbe Museum, but not before an unforgettable breakfast at Side Street Cafe, arguably one of the best cafes and restaurants in the entire state. From the live music to the outrageously delicious lobster rolls, this place makes other restaurants look average. There’s the Jesup Memorial Library, a fun space to browse the historical newspaper collection about the history of Bar Harbor.
Fairbanks, Alaska
Midnight Sun Festival in Fairbanks, Alaska. Image credit: Jacob Boomsma / Shutterstock.com.
You should visit Fairbanks, even if only once in your lifetime, especially because of the stuff that you will hardly find anywhere else. From grabbing a front-row seat to the northern lights to enjoying midnight sun in the summer, Fairbanks is like a story where truth is stranger than fiction. Alaskans may consider it big, but Fairbanks is home to just about 32,000 residents. The Fairbanks Ice Museum features interesting ice sculptures and slides, along with a nightly aurora show set in a vintage theater. If you are traveling with kids, one attraction stands out: The Fairbanks Children’s Museum. Expect orderly chaos with numerous options to keep the kids engaged, whether through easy crafts, painting sessions, building interesting structures, or simply enjoying the kids’ tree house.
Before the sun sets and the northern lights begin, work your way to the city’s downtown Golden Heart Plaza. You will find a statue that honours America’s “Unknown First Family,” but with a futuristic time capsule: 2059. If you have a culinary relationship with fried plantains steeped in authentic flavours, nab a chair at Eata Vybe Caribbean Cuisine, a centrally located Jamaican restaurant.
Oak Bluffs, Massachusetts
Historic gingerbread houses in Martha’s Vineyard, Massachusetts.
Oak Bluffs is a resort community tucked away on the northeast shore of the island of Martha’s Vineyard. One of the town’s best-known features is the Oak Bluffs Marina, the largest marina in the area and a long-time favorite of many boaters. Even if you are a first-time visitor, it will be difficult to miss Ocean Park, especially if arriving via the nearby ferry dock. You will find it an excellent spot to relax and watch the ocean on a nice sunny day. The best part is that it is close to the neighborhoods with all the colourful gingerbread houses. Meanwhile, The Sweet Life Café is an upscale spot with an ample wine list, while Flying Horses Carousel, the oldest operating carousel in America, offers hand-carved horses and a fun brass ring game. It originally operated as an attraction on Coney Island before being moved to Oak Bluffs in 1884.
Frankenmuth, Michigan
Frankenmuth, Michigan. Image credit Dennis MacDonald via Shutterstock.
You will need to pinch yourself here because you can easily be deluded into thinking that you are in some charming German Village by the Rhine. It is only that instead of the Rhine, you have the Cass River, a 61-mile-long rustic beauty that gives the town a mist of a countryside allure. Of course, Frankenmuth features the “world’s largest Christmas store.” Bronner’s CHRISTmas Wonderland is a shopper’s dream, the size of one and a half football fields. It boasts over 50,000 trims and gifts. There is Heritage Park, a peaceful place to stroll by the river, the highly rated Zehnder’s of Frankenmuth, which styles itself as “America’s Largest Family Restaurant,” and Frankenmuth Historical Museum, one of the best small-town museums in the Northeast with an on-site gift shop offering a variety of cool trinkets and souvenirs.
Portsmouth, New Hampshire
The historic Market Square in downtown Portsmouth, New Hampshire.
Portsmouth is a stunning harbor town with an eye-catching Market Square speckled with stimulating art galleries, bookstores, antique shops, and ethnic restaurants serving delicious cuisine. That said, Market Square is probably best known for its beautiful red brick buildings, many of which were constructed in the early part of the 1800s following a series of devastating fires. There is North Church, which has been a staple of the community from before the Civil War years, and the Strawbery Banke Museum, an evocative time capsule with homes built as far back as the 1600s. Some of the homes have guides and period actors. Also, the on-site gardens are incredibly beautiful and well-kept. As for live entertainment, the Music Hall Lounge is such an intimate venue with a great cocktail list and tasty small plates. There is Prescott Park as well, a breathtaking waterfront treasure in the area that accurately captures New England’s charm and beauty.
Cape May, New Jersey
Washington Street Mall in Cape May, New Jersey. Image credit JWCohen via Shutterstock
Cape May, the oldest beach resort in the nation, is at the southern tip of New Jersey. It was once widely associated with Mount Vernon, which, for a time, held the distinction of being the largest resort hotel in the United States. Today, Cape May’s charm is partly attributed to its concentration of more than 600 Victorian-style houses. Even by New England’s standards, that is quite a remarkable feat. There is the beach promenade, which spans more than a mile, the Cape May Lighthouse, whose history predates the birth of the new republic, and, of course, the widely popular Cape May Point State Park, whose dunes serve as vantage points for observing bird migrations along the Atlantic Flyway. Keep in mind that Washington Street Mall has a multitude of eclectic stores for everyone’s taste, while Il Riccio Cape May, just a few steps away, serves delicious zucchini spaghetti and some of the best gnocchi in the world.
Corning, New York
Rustic brick buildings and fall foliage along a street in Corning, New York.
If your view of the Empire State is largely informed by the choking crowds around Manhattan, it is time you explored the Finger Lakes Region of New York, a lush and lusty expanse with exceptionally clear lakes framed by vineyards and quaint towns. Corning is located south of Keuka Lake, one of the most picturesque in the region. Corning has been called “Crystal City” because of its glass-making heritage. The town’s signature attraction is the Corning Museum of Glass, and the downtown shops and restaurants play a role in the town’s highly acclaimed charm and allure.
Centerway Square features a vintage‐style clock tower along with benches, shade trees, and sparkling fountains. At the same time, the centrally located Rockwell Museum explores the evolving story of America through the eyes of artists. Meanwhile, Dippity Do Dahs Homemade Ice Cream, a few steps from the museum, serves intoxicating waffle cones and plenty of other flavorful offerings.
Amazing Town Squares To Explore
So, next time you schedule a vacation to the Northern United States, resist the temptation to head straight to your outdoor focus, whether a world-famous national park, a leaping cascade, or a glittering lake with a pretty beach. Several towns that you think are mere jumping-off points with nothing else to offer will instantly throw a surprise party your way. It is a stiff competition, but from Cape May to Corning, Fairbanks to Frankenmuth, many town squares in the Northern United States look fine-tuned for beauty and adventure.