11 Prettiest Towns in the Northern United States

The prettiest towns in the Northern United States stand out for their inclusive offerings of freshwater beaches, historic heritage, and an abundance of recreational outdoor activities. These charming northern towns offer some of the best well-rounded experiences, making them the perfect go-to destinations for first-time visitors to America. From the tight-knit community of Port Townsend to the artistic colony of Lenox, there is no wrong time to visit these beautiful destinations, as they offer year-round activities and entertainment for all interests. Promising travelers a warm, welcoming, and memorable time, here's a list of the 11 prettiest towns in the Northern United States. 

Bar Harbor, Maine

Opening the list of the prettiest towns in the Northern United States is a charming coastal town that makes almost every list of the most beautiful towns in America thanks to its vibrant nature. The city boasts both aquatic and green sceneries and makes for the perfect recreational small-town escape. From its Acadia National Park, known for its eye-opening fall foliage, to the serene crystal-clear waters, Bar Harbor brings visitors closer than ever to nature with its array of calming natural atmospheres. Put your outdoor skills to the test and indulge in various activities, from hiking to kayaking and surfing, when you visit Bar Harbor. Adding to the town’s aesthetic are quaint residential buildings of both wooden and brick structures that add a small-town feel to the city that enjoys an incredible nature-centric atmosphere. 

Stowe, Vermont

Stowe is a mountainous town that offers the best of every season yet stands out as the ultimate winter getaway nicknamed the Ski Capital of the East. The winter playground takes the setting of a lush green valley between the Green Mountains to the west and the Worcester range to the south. The town’s claim to fame is the Stowe Mountain Resort, a world-class ski resort with over 116 ski trails and 12 lifts, offering visitors a one-of-a-kind alpine experience without leaving the United States. Aside from the recreational aspect, the town is enhanced by its community events of festivals and its charming historic main street surrounded by acres of greenery. Visit the Vermont Ski and Snowboard Museum and support the town’s small businesses as you enjoy a truly American dining experience at local cafes and diners like Harrison’s Restaurant and Butler’s Pantry. 

Glasgow, Montana

One of the best-kept secrets in Montana, Glasgow, is named after the Scottish city and is known for its historical heritage and exceptionally calm environment. The Pioneer Museum of Valley County, with its fossils and Indian artifacts, along with the Charles M. Russell National Wildlife Refuge, are some of the many attractions in the area. Glasgow, Montana, is the definition of "A Town in the Middle of Nowhere," and there are very few surrounding communities, making it a peaceful haven and adding to its beauty. Zone out into peace and enjoy a local pint from Knuckle Brewery while you're at it. As quiet and isolated as any of the charming small towns on this get, you can spend your time roaming the area to view local arts at Art Spot and Sean Heavey Gallery or take the family down to the Children’s Museum of Northeast Montana and enjoy the popular World Wildlife Exhibit.

Mackinac Island, Michigan

Mackinac Island stands out as one of the most unique towns on this list for being a car-free island that takes pride in its well-preserved 19th-century buildings and vibrant downtown area. Mackinac Island is famed for its horse carriage rides, caramel corn, and Grand Hotel overlooking Lake Huron. Architecture enthusiasts are sure to enjoy the visit to Mackinac for the chance to cross one of the longest suspension bridges in the world, nicknamed Mighty Mac, and stroll the colorful downtown area abuzz with cyclers and horses. Satisfy your sweet tooth and try out the town’s finest fudges that became synonymous with the town and were popularized in the 1800s as a tourist’s delight when the island began developing a reputation of being a go-to vacation destination. Travel back to a time with less pollution and crowded streets, and embrace historic destinations like Fort Mackinac and Fort Holmes. 

Lake Placid, New York

Another nature-centric town that makes the list of the 11 prettiest towns in the Northern United States for being a haven for outdoor enthusiasts and being one of the only places in the world where the Olympics were hosted more than once. Set amidst the Adirondack Mountains, Lake Placid is known for being a winter sports capital and having over 29 named lakes, including Mirror Lake, which is named for its glassy surface in the winter. The town takes pride in its Olympic history and has developed a reputation of being a go-to destination to partake in almost any fun sport, from CrossFit training to Hockey and speed skating. 

Greenville, Maine 

Greenville, Maine, is one of the prettiest towns in all of the United States, not just its Northern Region. Costal wooden homes, crystal clear water, and abundant natural destinations give Greenville its romantic, cozy vibe. Hike the steep Big Moose Mountain, Visit the tucked away Spotted Cat Winery for a state of local production, and try to spot some Moose on your way at that Greenville is home to a large population. During your visit to Greenville, you'll also find a strong sense of local community with annual events like the Moosehead Family Village, where locals go to sell a range of handmade products, and The weekly Farmer's market that brings out all residents for fresh produce shopping. All that that the cool destination and moose spotting may sound like fun, but the number one must-do on your list should be viewing the town from up high with its many Seaplane tours Some of the most popular tours in the area include Currier's Flying Service and Jack's Air Service.

Decorah, Iowa

While each town on this list has its unique edge, Decorah balances all beautiful aspects in one place. Form a vibrant arts and cultural scene for all trout fishing and hiking recreational activities. WScenic natural beauty also plays a key part in the town’s character, boasting breathtaking valleys like those of Upper River Iowa that are decorated with cloud-reaching oak trees and narrow hike-able passages. The city embraces Scandinavian culture with its annual Nordic Fest, folk art, and historic building inspired by Norwegian-American culture. Visit The Decorah Vesterheim Norwegian-American Museum and explore surrounding buildings from earlier times, like the 1852 Egge-Koren House, the Rovang Parochial Schoolhouse, and the Painter-Bernatz Mill. 

Port Townsend, Washington

A quaint historic town on the Quimper Peninsula in Jefferson County, Port Townsend is known for its Victorian homes, warmhearted small-town feel, and beautiful nature. An explorer’s paradise, visitors will never get bored exploring the pretty Washington town from hidden abandoned bunkers like Fort Worden that narrate tales of the town’s past to waterfront parks that make up the ultimate picnic destination. Stroll the botanical wonders of Chetzemoka Park and spot roaming wildlife in the area, set up your tent and camo in Fort Worden State Park, and make your visit educational by visiting the Port Townsend Marine Science Center. Downtown Port Townsend is your go-to destination after a long day adventuring through the different atmospheres as you reward yourself and your loved ones with some fine dining at locally renowned restaurants like Finistère, Khu Larb Thai, and Hanazono Asian Noodle Soup. 

Lenox, Massachusetts

Lenox is a cultural hub in the Berkshires, known for the Tanglewood Music Festival, Lush gardens, rolling hills, and serene lush green parks. Although the Berkshires area is home to many beautiful, explorable destinations, Lenox stands out for its artistic heritage and a strong sense of community that can be experienced in places like the Boston Symphony Orchestra and its New England charm depicted through historic buildings like the red brick Ventfort Hall. Enjoy a one-of-a-kind entertainment experience at Shakespeare & Company, known for being one of the Largest Shakespeare festivals in the Country; learn about railroad history at Berkshire Scenic Railway Museum, and stop by the Norman Rockwell Museum.  

Grand Marais, Minnesota

Grand Marias is a charming harbor village on the shores of Lake Superior and is home to a small population of 1400 residents. The town perfectly represents an ideal mind-calming escape with its tree-lined freshwater lake, tranquilizing harbourfront, and wholesome local art scene like the annual Plein Air Grand Marai. Zone out into the great outdoors when you like the 50-mile Superior Trail located just outside the town, or charter a boat for some of the best views, and don’t forget to visit the old Instagrammable Grand Maraia lighthouse, one of the best-known landmarks in the area. In addition to all these charming advantages qualifying Grand Marias to make the ultimate list of the prettiest towns in the Northern United States, the city is well-known for having some of the darkest skies in the area, so don’t forget to look up at night during your relaxing visit to Grand Marais. 

Woodstock, Vermont

Wrapping up the ultimate list of the prettiest towns in the Northern United States is the quintessential New England town of Woodstock, Vermont, boasting 18th-century buildings, scenic beauty, and Luxurious resorts that make for an unforgettable visit. Must-see historic places in town include Marsh Billings Rockefeller National Historical Park, Billings Farm and Museum, and the Norman Williams Public Library, built in 1883. Stay and dine at local upscale businesses like the Village Inn of Woodstock, Lincoln Inn & Restaurant at the covered bridge, and The Prince & The Pauper Restaurant.

The geographical setting of America's Northern towns allows for a diverse experience that ranges from world-class ski resorts to live entertainment like the Shakespeare festival in Lenox. In addition to this inclusive list, you rarely encounter a Northern town that will disappoint you thanks to the area's abundant nature, friendly locals, and early development history.