Day 5: Scranton, PA, to Maine: Soak up brunch at JJ McNally’s before hitting the road because your options are limitless today: you could stop in Portland, ME, after only seven hours, or continue all the way to the Canadian border in 12 hours. Whatever your decision, the day begins with I-84 east through the Poconos into New York, then across the Hudson River into Connecticut. History abounds as you drive through Danbury, which was settled in 1685, then Waterbury (1674), New Britain (1687), then Hartford (1623). That history is updated at On20, however, where mouth-watering American food meets sweeping views of the Connecticut River from the 20th floor of One State Street.
Back on I-84, you’ll enter Massachusetts, where can bypass Boston via I-495. At the Merrimack River, take 1A east to the Atlantic Ocean and hug the Seacoast through Hampton, NH, into charming Portsmouth, with its intimate downtown, clapboard houses dating to the 1700s, and a naval shipyard that maintains a link to the area’s salty past. Crossing the Piscataqua River on US 1, head east through Kittery on Highway 103 to stay close to the coast, then blaze your own path on Highways 1, 1A, 9, and 77 as you near Portland. Considered one of the United States’ most underrated cities, you could easily end your trip here exploring the multitude of restaurants, bars, art galleries, and lighthouses that dot this gorgeous slice of the Eastern Seaboard. Or you could keep heading north to the Pine Tree State’s vast northern wilds: Penobscot Bay, Acadia National Park, Mt. Katahdin, Presque Isle. Extra credit? Drive into the Canadian Maritimes, get lost on the New Brunswick-Prince Edward Island-Nova Scotia loop, and vow to never leave. It’s just that beautiful.