10 Prettiest Small Towns In The Northern United States
Road trip enthusiasts tend to fall into two groups. One researches the most visited tourist destinations and sets a route accordingly. The other sees the trip as a journey rather than a destination and looks for unique and beautiful spots off the beaten path. The good news is that plenty of places please both kinds of travelers. The prettiest small towns across the northern US reward coastal wanderers, Great Lakes explorers, and mountain seekers alike, so your next road trip can be everything you imagine.
New England - Maine, Vermont, and New York
Bar Harbor, Maine
Ocean views and a welcoming atmosphere make Bar Harbor, Maine a high-ranking choice for tourists. It is indescribably decadent to enjoy seafood likely snatched the same day from the cool New England waters. If the seafood is not enough to tantalize your taste buds, know that Maine is well known for its wild blueberries, which are expertly crafted into luscious pies, ice cream, and desserts. Great eating is not the only draw. There are also sights and activities galore, including puffin tours, whale watching, and other ocean adventures. The beauty of the town itself cannot be ignored either, with plenty of historic mansions to remind you of the gilded age this area enjoyed in a bygone era. Outdoor enthusiasts enjoy Bar Harbor because of Acadia National Park's hiking trails.
Woodstock, Vermont
Woodstock, Vermont should not be confused with Woodstock, New York, whose name was borrowed for the 1969 music festival that actually took place on a farm in Bethel, roughly 60 miles away, and drew over 460,000 people. Woodstock, Vermont has its own long history. This town was chartered in 1761, which is 15 years before the US even declared its independence. As an older town, it has moved through many architectural styles. A stroll through Woodstock will be met with Queen Anne, Greek Revival, Georgian, and Federal architecture. Covered bridges are also seen here, including the Taftsville, Lincoln, and Middle covered bridges. A great time to visit is during the annual Wassail Weekend, which has been held for more than 40 years. Woodstock turns into a winter wonderland each December with twinkling lights, live music, a parade, horse-drawn carriage rides, a holiday market, and many other special events. It is a time when Woodstock is at its prettiest.
Cold Spring, New York
There was a time in US history when the steam engine was king, and Cold Spring, New York was instrumental in its production throughout the 19th century. The town sprung up around the West Point Foundry, where not only steam engines but also artillery was fabricated. Its location on the Hudson River was critical for shipping in materials and shipping out finished products. Today the Foundry is a 90-acre outdoor museum showcasing the history of Cold Spring. The town is historically significant for its Civil War activity, and for the contemporary Italian art that became a focus after the war. Of course, the river lends itself to a variety of water activities, including waterfront walks, kayaking, paddleboarding, and picnics. Whether one chooses Cold Spring as a stop along a road trip or a destination reachable by train from New York City's Grand Central Terminal, this pretty town and its many seasonal events are sure to please.
Great Lakes/Midwest - Michigan, Illinois, Minnesota, Wisconsin
Mackinac Island, Michigan
Is it really part of a road trip if you head somewhere cars have been banned for more than a century? Well, yes, if you make Mackinac Island, Michigan a stopping point. Take a ferry or airplane onto the island, then get around on foot or by using the island's bicycles and horse-drawn carriages. Imagine relaxing without the sounds of traffic, and you will have a good idea of what makes Mackinac Island a wonderful place to visit. The state park takes up 80% of the island, and its natural beauty is perfect for hiking, horseback riding, and biking, all without worry of vehicles getting in your way. The downtown is the place to go for unique local shops, dining options, and places to stay.
Galena, Illinois
The lively downtown and well-preserved 19th century architecture are the main draws of Galena, Illinois. Native Americans enjoyed this area a thousand years before the country was colonized. They found the ore called galena here and made body paint with it for use in burial rituals. The town later adopted the name of the ore. Galena has been a popular town for quite some time, as nine Civil War generals called it home, including Ulysses S. Grant. When galena, a form of lead, fell out of favor, the town lost its boomtown status and turned to tourism to boost its economy. That is good news for travelers, because it has resulted in a pretty town with plenty to do. Enjoy the red trolley ride through downtown and gaze upon the plethora of red brick buildings. Hop out along the way to enjoy the brisk pace of shops, cafes, wineries, and boutiques. In addition, there is an event going on nearly every month.
Grand Marais, Minnesota
There is nothing quite like a harbor village for relaxation, outdoor recreation, and friendly people. Grand Marais, Minnesota is just that sort of place. This artsy harbor town delights the senses with its natural beauty and lively art scene. The Ojibwe people populated the area before colonization and named it Gichi-biitoobiig, which characterizes it as having two bays. They used the area primarily for wild rice harvesting and summer fishing. Fishing has been a big part of the history of Grand Marais, but even commercial fishing was no match for the tourism that began because of the beauty of the area. The many cultural events held showcase the history and the use of its natural resources. Examples include the Fisherman's Picnic, Moose Madness, and the Grand Marais Arts Festival. The historic downtown includes sights such as the 1896 Lightkeeper's House and the 1944 Bally Blacksmith Shop.
Bayfield, Wisconsin
Bayfield, Wisconsin is located on Lake Superior. Its fishing and timber resources made it popular initially, and being on the lake afforded the ability to ship those resources to other coastal towns and cities, such as Cleveland, Buffalo, and Chicago. Its natural beauty was not lost on those who settled here, and they took steps to ensure the preservation of its history. While being a lakeside town contributes to its appeal, the historic downtown looks like it was trapped in the Victorian era. A prime example is the Old Rittenhouse Inn, a red Queen Anne landmark with a wraparound porch. The many shops, art galleries, and cafes take you back in time.
West Coast/Mountains - Colorado, Montana, Wyoming, Washington
Telluride, Colorado
Telluride, Colorado is one of those places people often first visit for the alpine skiing and end up absolutely falling in love with everything else. It does not matter if the mountains are covered in snow or not, the beauty is remarkable and adventure is found throughout the year. Nature is not the only draw. The Victorian-era architecture, the unique galleries and shops, the numerous festivals throughout the year such as the Telluride Film Festival, and a free gondola ride all make Telluride worth a visit. Speaking of the gondola, nothing goes to waste in Telluride. The gondolas that were retired were turned into unique cabins for dining and art displays in Mountain Village.
Whitefish, Montana
What is not to like about a mountain resort town with amazing skiing, a walkable downtown, and a 7-mile-long freshwater lake? Whitefish, Montana seems to have it all when it comes to natural beauty and outdoor recreation. Beauty is all around, as Whitefish is surrounded by the Rocky Mountains. Just 20 miles from the west entrance to Glacier National Park, there is no limit of hiking and forest enjoyment. Native American history buffs will enjoy learning about the Kootenai and Salish tribes. Whitefish grew up as a Great Northern Railway town in the early 1900s and became a gateway for visitors heading to nearby Glacier National Park. The 1947 opening of Whitefish Mountain Resort, originally Big Mountain Ski Area, turned tourism into the town's main economic driver. The combination of native and cowboy heritage makes Whitefish rich with history.
Jackson, Wyoming
Take a step back in time and experience traditional cowboy western ambiance. Jackson, Wyoming, with its wooden boardwalks, famous antler arches, scenic tram, and stagecoach rides, has much to offer that is different from many mountain towns. It is located just south of Grand Teton National Park and has tremendous views of the Teton Range. The Teton Village ski resort offers activities throughout the year. Adrenaline seekers can do things like downhill mountain biking after getting a ride to the top on a ski lift, or real rock climbing. The National Elk Refuge is next to Jackson and affords the chance to see these magnificent creatures. In the winter, you can also take a sleigh ride and observe wandering elk. For a more comical wildlife display, consider stopping by the Jackson Mercantile to check out some quirky taxidermy.
Leavenworth, Washington
Imagine experiencing a Bavarian village atmosphere without traveling abroad. That is what you can enjoy with a trip to Leavenworth, Washington. A unique Bavarian feel comes complete with schnitzel, beer, cider, and all the things that will transport you to southeast Germany. It goes without saying that a perfect time to visit is during the Oktoberfest festivities, but there really is no bad time to head to Leavenworth. One of the most attractive things about Leavenworth is the immersive experience on a scale pretty much unheard of elsewhere. The vibe captures you and does not let go until you leave. Surround all of that with the beauty of the Cascade Mountains, and there is nothing like it.
Your Northern Road Trip Awaits
It is said that beauty is in the eye of the beholder, but it is a safe bet that few people would argue that these small towns are not among the prettiest. The most populated among them is Jackson, Wyoming, with almost 11,000 residents, so they all keep the small-town atmosphere that so many travelers enjoy. Even so, they have plenty to do, which means the destination traveler will be just as pleased. Traveling across the northern US and including stops at as many of these towns as possible would make for an amazing road trip.
