6 Whimsical Towns to Visit in the Northern United States
Pack your bags for a whimsical journey through the most charming and quirky small towns in the northern United States. From the Bavarian-themed streets of Leavenworth, Washington, to the seaside charm of Bar Harbor, Maine, these towns have unique festivals, historic landmarks, and one-of-a-kind local traditions. Explore the Gaslight District in Petoskey, Michigan, hunt for 350-million-year-old stones along the shores of Lake Michigan, and dive into winter festivities in Whitefish, Montana. Whether it is Oktoberfest in Leavenworth or a strawberry festival in Cedarburg, these towns in the Northern United States are full of character and fun in spirit.
Cedarburg, Wisconsin
About 20 miles north of the city of Milwaukee, or “Brew City,” visitors will discover the charming small town of Cedarburg, Wisconsin. Known for its whimsical events like the Cedarburg Strawberry Festival and the Wine & Harvest Festival, which are held annually, this town is a fun small spot to experience. History buffs will enjoy wandering through the Cedar Creek Settlement, a collection of 19th-century limestone buildings along Cedar Creek now filled with art galleries, shops, and restos like the Anvil Pub & Grille and the Lakeside Cookie Company. Constructed in 1864 as a woolen mill that was a major supplier of woolen blankets for the war effort, the mill now houses the Cedar Creek Winery.
Wisconsin was once home to more than 40 covered bridges, but today, the sole survivor is the Cedarburg Bridge (known as the “Red Bridge”). Visitors to Cedarburg can see the historic bridge in Covered Bridge Park, whose original span measured 120 feet long by 12 feet wide and made from pine logs. Spend time in the park near the fairytale bridge, where birding, kayaking, and picnicking are all popular pastimes.
Frankenmuth, Michigan
Willkommen to Frankenmuth, also known as “Michigan’s Little Bavaria,” with its fairy-tale-inspired buildings and old-world vibe. Reminiscent of a traditional German village, the small town sits on the Cass River, where visitors can enjoy a narrated tour of Frankenmuth aboard the 150-passenger authentic paddlewheel riverboat, the Bavarian Belle. Nearby, visit the River Place Shops, a German-themed outdoor shopping mall that hosts the world’s largest Olympic-style festival for dogs every year, the famous Frankenmuth Dog Bowl.
The small town is also renowned as home to one of the world’s largest Christmas stores, Bronner’s. The holiday shop is so massive that store employees hand out maps to help customers navigate the space 1.5x the size of a football field. Visitors to town can’t miss a stop at the family-owned, 1968-era Frankenmuth Cheese Haus, which carries over 270 varieties of cheese from around the globe and cheese made “in haus.” Finally, no day trip to little Bavaria is complete without a pint at Michigan’s oldest microbrewery, the Frankenmuth Brewery.
Bar Harbor, Maine
Bar Harbor, Maine, is the gateway to the beautiful Acadia National Park, a popular destination for adventure travelers from all over the world who come to trek the over 150 miles of hiking trails in the park. The trails range from easy scenic walks to challenging summit hikes up Cadillac Mountain—the highest point along the North Atlantic coastline at 1,530 feet. Other areas in the park worth exploring include the whimsically named Thunder Hole, a small cavern at the bottom of an inlet where the crashing waves create a booming sound, the famous rung and ladder trail called the Beehive Loop, and the iconic Bubble Rock.
Bar Harbor has plenty of seaside charm, dotted with colorful boats, classic New England cottages, and quirky coastal shops like Cool As A Moose, A Little Mad, and Debbahs Clothing & Gifts. No trip to lobster-loving Maine is complete without chowing down on a crustacean or two at lobster shacks like Stadium, the Travelin’ Lobster, or the Trenton Bridge Lobster Pound.
Leavenworth, Washington
Two hours east of Seattle, visitors are often surprised to discover themselves in the Bavarian-themed village of Leavenworth. Tucked in the Cascade Mountains, full of alpine architecture, flower boxes, and festivals galore, Leavenworth bills itself as America’s “unofficial Bavarian capital.” For three weekends in October 2024, Leavenworth welcomes residents and visitors downtown to celebrate Oktoberfest with longstanding traditions of music, dancing, and keg tappings with local breweries like Icicle Brewing Co., Blewett Brewing, and Doghaus Brewery. For kids, there is a Kinderplatz with a 62-foot Ferris Wheel, activities, and a “rootbeer” garden.
In late November, the town transforms itself into Christmastown, a winter wonderland lit with over half a million sparkling bulbs illuminating the village from 6 AM until 11 PM until the end of February. Wander through the pretty streets and visit one-of-a-kind shops like Kris Kringl, Schocolat, and the Magical Hippie Crecallium—a cosmetics boutique inspired by glistening dewdrops and fluttering fairy wings. Be sure to visit the Leavenworth Nutcracker Museum, a quirky attraction that houses over 9,000 nutcrackers crafted in 50 countries worldwide.
Petoskey, Michigan
Aside from its namesake, fossilized coral stones known as Petoskey stones, the town of Petoskey, Michigan, is known for its beautifully preserved Victorian-era buildings and historic Gaslight District. Lit by iconic gaslight-style street lamps, the district gives the city a storybook Sherlock and Holmes atmosphere with plenty of specialty shops, casual cafés like North Perk Coffee, and fine dining restaurants Chandler’s, a restaurant, and Pour Kitchen & Bar to choose from.
The Petoskey Stone has been Michigan’s state stone since 1965, and collecting them is a much-loved pastime. The distinctive hexagonal patterned rocks are plentiful along the shores of Lake Michigan and are often polished and used in jewelry. The hot spot for stone hunting in town is the 25-acre Bayfront Park along Little Traverse Bay, the Petoskey Breakwall, and Petoskey State Park.
Whitefish, Montana
Whitefish is a mountain resort town only 50 miles from the border between the United States and Canada. It is a ski town, home to the Whitefish Mountain Resort, one of Montana's most popular ski resorts. The lively après-ski scene gives the town a carefree, fun-loving vibe during the cold winter months. The annual Whitefish Winter Carnival kicks off with a Penguin Plunge into a hole carved into the icy waters of Lake Whitefish, followed by parades, beer barters, snow sculptures, street dances, and a celebration of Ullr, the Norse god of snow.
The town is also mildly obsessed with huckleberries, and visitors are invited to forage for huckleberries between late July and September. There is an annual Huckleberry Days Festival, and visitors can be sure to find huckleberry jam at the Wild Coffee Company, ice cream at Sweet Peaks Ice Cream, and even huckleberry vodka at Spotted Bear Spirits.
Uncover the delightful and often quirky aspects of these six small towns. From unique local festivals and charming historic districts to playful traditions and popular attractions, these towns offer a refreshing break from the ordinary. Whether celebrating the Ullr Festival in Whitefish, Montana, or exploring "little Bavaria" in Frankenmuth, finding whimsy is about embracing the unexpected and enjoying the playful, imaginative elements that make each town special.
