Highways and History of the Midwest: Chicago & the Upper Midwest
Itinerary - New England Shores and Cities
Regional Suggestions Boston | North Shore | Maine
White Mountains | Vermont

About this itinerary

Driving distance: 477 Miles
Recommended travelling time: 15 Days
Recommended travel season: Year-round destination
A lively, contemporary city that embraces its history, Boston, Massachusetts, is also the gateway to all that New England offers, including charming villages, a rugged coastline, and a thriving culinary scene.

Boston, Massachusetts


Although many visitors know about Boston's rich history and its role in the Revolutionary War, they may not be aware of the city's world-class museums, numerous universities and abundant shopping opportunities. Begin your exploration of the city on The Freedom Trail with its 16 historic stops, and visit the many museums, Harvard University and Fenway Park. If the weather is nice, stroll through the Boston Common and the Public Garden.
To next stop: 40 miles| Total distance travelled: 0 miles


Massachusetts' North Shore

Take a break from the city and head north to Cape Ann's rustic maritime towns, artist colonies and scenic beaches. In Gloucester, centre of the local fishing industry, dine on fresh seafood with scenic harbor views. In the picturesque town of Rockport, stroll to explore small art galleries, gift shops and informal seafood restaurants. Stay in a historic inn and explore quiet beaches and lighthouses.
To next stop: 117 miles | Total distance travelled: 40 miles


Just a couple of hours north of Boston, Maine makes for a wonderful multi-day excursion. In Portland, Maine's largest city, head out on a whale-watching tour, enjoy a harbour cruise, eat at a rustic seafood 'shack' or take part in a lobstering trip. Explore the cobblestone streets of the Old Port Historic District, which overflow with nightlife on weekend evenings. Farther north along Maine's rugged coast, quaint Bar Harbor is an excellent jumping-off point to stunning Acadia National Park.
To next stop: 235 miles | Total distance travelled: 157 miles


White Mountains, New Hampshire

Drive up, up, up (or take the cog railway) for breath-taking views at the top of towering Mount Washington, the highest peak in the east. Hike through the Flume Gorge, a spectacular natural chasm with waterfalls and covered bridges. In autumn, enjoy harvest farm festivals and mountainsides covered with brilliantly coloured leaves. In winter, skiing and other snow sports are popular.
To next stop: 85 miles | Total distance travelled: 392 miles


Just to the west of New Hampshire lies pastoral Vermont, with rolling mountains, scenic valleys with white church steeples, picturesque bike trails and popular ski resorts. Taste the state's abundant harvest at farm-to-table dinners and shop for maple syrup, artisanal cheeses and locally produced wines.
Total distance travelled: 477 miles

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Some map icons by Scott de Jonge, used under CC 3.0 BY  Train vecotr by Freepik

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