An American road trip from Boston to Chicago

There’s nothing more American than a road trip. Here are five places you can’t miss on your journey between two great destinations: Boston to Chicago.

Adirondack Mountains

About four hours from Boston, take a break and embrace nature at the Great Sacandaga Lake, one of the Adirondack Mountains’ largest lakes measuring 29 miles long and up to five miles wide. A very popular vacation and camping destination, the lake is ideal for outdoor adventure, of course, offering plenty of options during every season. If you can’t lug camping gear with you, get a hotel room at any of the nearby towns of Broadalbin, Edinburg, West Day, Conklingville, Batchellerville, Fayville and Fish House, among others, and enjoy the north’s rustic charms before continuing west on your journey.  

Old Erie Canal & Seneca Falls 

A three-hour drive west brings you to the Old Erie Canal State Historic Park, in East Syracuse, N.Y., which at first glance may not be draw-dropping alluring, but is an important historic and geographic site which connected the East Coast with the Midwest through trade and travel in the 1800s. The park encompasses a 36-mile segment of the original, iconic Erie Canal, and also includes restored segments of the canal’s waterway and towpath which were in active use between 1825 and 1917. The resurfaced towpath is great for biking and hiking, or if you have a canoe or kayak on hand, you can cruise down the canal like it’s 1862.

Nearby, visit Seneca Falls, N.Y., a fascinating city with deep roots in social and religious reform. In the 1800s, supporters of the Underground Railroad were very active here and the area became a hotbed of anti-slavery activism in the years preceding the Civil War.

Arguments for women’s rights would come from experiences in the anti-slavery movement, and in the mid-1800s, the Women’s Rights Movement officially began here with the first Convention on Women’s Rights at the Wesleyan Chapel on Fall Street. The Women’s Rights National Historical Park embodies the movement: Guests can visit the first Women’s Rights Convention site and the Elizabeth Cady Stanton House, the National Women’s Hall of Fame and more.

Niagara Falls

Get back out into the sunshine at the legendary Niagara Falls, straddling the international border between Ontario, Canada and New York State. It may be a tourist trap but it’s one you have to visit at least once in your lifetime, right? Niagara is actually made up of three different waterfalls—Horseshoe Falls, American Falls and Bridal Veil Falls—which, unsurprisingly, make up the biggest falls in North America. For an adventurous spin on the experience, hop onto one of the many ferries which explore the Niagara River below. You’ll get so close to the base of the falls that you’ll definitely get drenched—a nice road-trip wake up, right? 


Next, sidle on over to Cleveland, Ohio, after a three-and-a-half-hour drive, for a taste of some of America’s greatest music throughout the decades. Cleveland is most notably home to the Rock & Roll Hall of Fame, which is located downtown on the shore of Lake Erie. Why is this place so important? Because it documents the best-known and most important artists and influencers in the rock and roll industry. Most recent inductees into the Hall of Fame for this year include Bon Jovi, The Cars, Dire Straits and The Moody Blues. 


Despite its notoriety for suffering from severe urban blight, this city, nearly three hours west of Cleveland, is undergoing a renaissance with young entrepreneurs at the helm. Lonely Planet has named it the world’s second-best city to visit in 2018. LP says that young creative types jump-started the scene when they began transforming the slew of abandoned buildings into distilleries, bike shops and galleries, which prompted more positive change like the construction of parks, sports arenas, hotels, and more. Plus, something significant was born here besides 20th-century mass automotive production (think Ford, Chrysler, etc.). Here, Motown music took the world by storm, and you can visit the Motown Museum which was originally the recording studio and residence of producer Berry Gordy and Motown Records. 

After nearly five more hours on the road, you’ll reach Chicago where, if you’re ready for it, a new adventure begins.  

Planes, trains and automobiles, an American road trip doesn’t need to be a full circle. Fly to one city and drive to the next.

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