13 Most Charming Cities in the Northern United States

In common communication, the United States is divided into five different regions, and they all enjoy slightly different climates, cultures, and economies. Northern states, including the northeast and some midwest regions, are home to unique climates influenced by the Pacific Ocean, lakes, and mountains. Major cities in the northern region of America are known for their diverse communities, booming business potential, and the perfect balance of weather throughout seasons.

Most of these suggested charming cities offer great relocation opportunities and a range of different outdoor activities. Many cities in states, such as New York, New Jersey, Pennsylvania, and Rhode Island, have a unique history of being one the first destination for settlers due to their strategic location. 

Milwaukee, Wisconsin

Aerial view of the homes along North Wahl Avenue in Milwaukee Wisconsin
Aerial view of the homes along North Wahl Avenue in Milwaukee Wisconsin

Rich in American culture, Milwaukee, Wisconsin, is a mix of everything that makes up the American dream, from sandy sunny shores to skyscraping buildings and historical attractions. Located on the shorelines of Lake Michigan, Milwaukee is the largest city in Wisconsin by population and offers something for everyone and a perfectly mild climate all year round. The town is mainly known for its local breweries and the Milwaukee Brewers baseball team, but that’s certainly not all there is to the city. Visit a range of historic and niche museums, such as the Harley Davidson Museum and the Milwaukee Art Museum, and enjoy the city’s many parks. 

Portland, Maine

Portland Cathedral of the Immaculate Conception at 307 Congress Street in downtown Portland, Maine
Portland Cathedral of the Immaculate Conception at 307 Congress Street in downtown Portland, Maine

Portland is a go-to for every resident of Maine, as it portrays the beauty of Maine in a busy city with lots to do. There is never a wrong time to visit the city, as it is rich in cuisines and cultures and has outdoor activities for every season. The main element that makes Portland stand out is its vibrant historic downtown with romantic cobblestone streets. Enjoy everything from watersports and lively nature to live music venues and old iconic restaurants and cafes such as The Porthole, which was established in 1929.

Burlington, Vermont

Burlington, Vermont, USA at Church Street Marketplace
Burlington, Vermont, USA at Church Street Marketplace

Sitting on the coast of Lake Champlain south of the Canadian border, Burlington is the perfect place to visit for an artistic experience and nature-centric trip at its many attractions, such as the Waterfront Park and North beach park located on the city’s north end. Burlington is big on bike paths, hiking trails, and more, but nothing is as symbolic as Chruch Street and Main, where all events happen, and a range of locally owned businesses add their own touch of what the city means to them.

Providence, Rhode Island

Skyline of Portland, Maine
Skyline of Portland, Maine

Located in the smallest state with the longest name, Rhode Island rarely makes any list of the best places to visit unless you’re trying to experience something out of this world. Rhode Island is home to the original Conjuring house, the Big Blue Bug Nibbles in Providence, and many shipwrecks over time. Although Providence is home to the world’s largest bug, it also boasts beautiful green landscapes and crystal clear waters. Its downtown is decorated in breathtaking extra-large murals and has some of the best seafood cuisines in the area. Providence River crossing its city center adds to its beauty and magnifies the city’s natural element. 

Madison, Wisconsin

Madison skyline and Wisconsin State Capitol
Madison skyline and Wisconsin State Capitol

Home of the Wisconsin State Capitol building, Madison is one of the most charming cities on this list of the best cities in the northern United States for its breathtaking State Street overseeing the Capitol building. Start your journey in State Street by visiting the Mall library adn make your way down to find a range of diverse cuisines, fashion shops, and nightlife. Additionally, one of Madison’s best places to visit is the Memorial Union Terrace for live music events while chilling on the shore of Lake Mendota. 

Philadelphia, Pennsylvania

Independence Hall in Philadelphia, Pennsylvania
Independence Hall in Philadelphia, Pennsylvania

Commonly referred to as Philly by state locals, Philadelphia is the second most popular city in the Northeast megalopolis and Mid-Atlantic regions after New York City. The city’s history dates way back to being the nation’s temporary capital from 1790 to 1800. The breathtaking Victorian architecture blends in flawlessly with the modernized city buildings balancing a tale of two significant and impactful eras. Tour the independence hall, visit the liberty bell, and eat all you can from various vendors at The Reading Terminal Market. Finally, you can’t say you’ve been to Philly without trying an Authentic Philly Cheesesteak sandwich. 

Chicago, Illinois

Chicago skyline aerial drone view from above, lake Michigan and city of Chicago downtown skyscrapers cityscape bird's view from park, Illinois
Chicago aerial view from above, with Lake Michigan and the city of Chicago

No list of northern best cities is complete without including Chicago, or as locals call it, the “Windy City.” from top-tier shopping destinations and restaurants to abstract architecture, the city isn’t the most affordable but is definitely worth checking out. Enjoy some Deep-Dish Pizza and go site-seeing to visit beautiful symbolic attractions such as Buckingham Fountain, The Navy Pier, and a range of world-renowned museums. Additionally, the best views of the city’s unique architecture are from the Chicago River, crossing the city's center and spanning over 40 miles north of the downtown loop area.

Billings, Montana

A road winds through Billings Montana
A road winds through Billings Montana

Shaped by the Yellowstone River and sheltered by the Rims, Billings is a regional hub for commerce. Billings is Monana’s most populous city and the place to be for adventurous escape and outdoor activities. They nicknamed the city between rim rocks due to the yellow stones surrounding many of its banks. Visit Yellowstone Park, take hiking tours, and enjoy unique cave kayaking at Pictograph Cave State Park, 5 miles south of the city. Visitors can also learn about the city’s history and its significant role as a railroad city at Billings’ many historical museums. 

Pittsburgh, Pennsylvania

Downtown skyline of Pittsburgh, Pennsylvania at sunset
Downtown skyline of Pittsburgh, Pennsylvania at sunset

Known for its many breathtaking bridges, Pittsburgh was nicknamed the “Steel City” for its mass production and significant role in steel manufacturing. Pittsburgh today is one of the must-see places in northern America. Pittsburgh is in the middle of three large bodies of water: the Monongahela, Allegheny, and Ohio Rivers, and is nicknamed the City of Bridges. Some of the best destinations to visit include the Phipps Conservatory botanical gardens, mount Washington, and the strip district for street vendors, local shops, and more.

Syracuse, New York

Downtown Syracuse New York with view of historic buildings and fountain at Clinton Square
Downtown Syracuse New York with view of historic buildings and fountain at Clinton Square

Syracuse is a popular relocation destination for its affordability and strategic location near the big apple. The city is known for its Canadian-like weather due to its proximity to “The Great White North,” Located 244 mi from Toronto, Ontario. Aside from being one of the best relocation destinations and its proximity to Toronto and New York City, Syracuse is home to many colleges and universities, such as Syracuse University and Le Moyne College. Despite being a snowy city in the winter, Syracuse is full of life and color, making it the perfect go-to for summer or winter activities. 

Rochester, New York

Skyline of Rochester, New York
Skyline of Rochester, New York

The perfect balance of a little bit of everything in one city, Rochester is home to many nature sceneries, beautiful parks, historic buildings, and museums that narrates the city’s history as a productive forest-decorated city. When in Rochester, NY, visit lake ontario beach, and check out some of its many waterfalls, such as the Upper or High Falls, the Middle Falls, and the Lower Falls. The George Eastman Museum is the world’s oldest museum dedicated to photography and is located in the home of George Eastman, the founder of the Kodak Company.

Jersey City, New Jersey

Exchange Place, Jersey City, New Jersey skyline
Exchange Place, Jersey City, New Jersey skyline

A picturesque metropolis nestled on the banks of the great Hudson River and the second most populous city in the state of New Jersey. One of the most diverse cities in the U.S., JC is home to a historic downtown, Liberty State Park, and fun water tours. Additionally, Jersey City is one of the best places to live in New Jersey, with picturesque state parks, marvelous skylines, world-class shopping malls, and fun-filled amusement centers.

Ann Arbor, Michigan

Aerial View of Downtown Ann Arbor, Michigan in summer
Aerial View of Downtown Ann Arbor, Michigan in summer

Finally, Ann Arbor, known as Tree Town, makes up the best city in the state of Michigan, inheriting Canadian greenery and the forest-covered city aesthetic. Ann Arbor is known to be home to University of Michigan, but aside from being the student go-to, it boasts a beautiful historic downtown that gives off classy 80s and 90s vibes with its vibrant, locally owned stores and brick walls. 

Ultimately this list of the most charming cities in the northern United States offers a wide range of the best cities to visit, relocate, or plan a road trip to. From history to shopping, and outdoor activities, these major cities have something for everyone; visitors will immediately feel homely. Yet the best thing about these northern American cities is that they balance a contemporary lifestyle emphasizing its natural beauty. Shop major labels and brands, immerse yourself in true American history embellished with modernization, and find your new favorite city. 

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