Summer is here which means it’s the perfect time to take a New England road trip! Enjoy cool summer nights, plentiful outdoor activities and some much-needed relaxation surrounded by New England’s beautiful coastal scenery. As a centralized location and major airport hub, we recommend starting your trip in Boston.
Day 1 – Start Your Road Trip in Boston, MA
Start your trip learning about the incredible history of this coastal town founded in 1630. Get to know the city on foot by joining the famous Freedom Trail daily tours. The 2.5 mile-long walking tour takes you to 16 historical sites including museums, churches, burial grounds, parks and the U.S.S. Constitution. Then, enjoy lunch on Newbury Street, located in Boston’s prestigious Back Bay neighborhood. The area is renowned for great shopping and a plethora of cafes. Stroll through the manicured lawns of the Boston Public Garden where you’ll see the Make Way for Ducklings sculptures and great views of the city.
After a long day of walking, it’s time to relax in the North End, Boston’s famed Little Italy. With so many boutique Italian eateries to choose from, we recommend mouthwatering, homemade pasta paired with a glass of red wine at Carmelina’s. For dessert, try the original Boston Cream Pie in Parker’s Restaurant at Omni Parker House, famed as the creator of both the Parker House Rolls and the Boston Cream Pie. If you’re looking for nightlife, fans of jazz music and craft cocktails will want to check out Beehive Boston.
Day 2 – New England Road Trip to New Hampshire
Head up I-95 towards Kennebunkport, Maine. Known for its beaches and historical sites, this small town is a nice place to pull over and stretch your legs. Visit the Seashore Trolley Museum to explore how trolleys transformed the lives of Mainers, and kids will especially enjoy riding the electric trolleys. Stroll through the quaint downtown, and enjoy a fresh lobster roll at the casual town favorite, The Clam Shack.
Head inland towards Bretton Woods, New Hampshire, just 2 1/2 hours north. Driving through White Mountain National Forest, you’ll enjoy mountain views, fresh air and wildlife. The forest is home to the highest peaks in the North East. Settle into your lodging at Omni Mount Washington Resort, a member of The Historic Hotels of America next to Mount Washington. As one of the last Grand Dames in the area, the resort has hosted countless U.S. presidents and historical figures. Indulge in resort dining, the world-class spa or a picturesque round of golf. Nearby the resort, you can explore the 7.2-mile Champney Brook Trail near Conway, New Hampshire or take a swim in the natural waterfalls at Franconia Falls.
Day 3 – South to Providence, Rhode Island
When it’s time to hit the road again, head south to Providence, Rhode Island. On your way down I-93, stop for a few hours in historic Concord, Massachusetts to visit a number of historical sites. As the setting for the start of the Revolutionary War, the Minute Man National Historical Park celebrates the story behind the Battle of Lexington and Concord. In the 19th century, literary heroes like Emerson and Hawthorn came here for inspiration. Get inspired yourself at Louis May Alcott’s Orchard House, the set of her famous novel Little Women, or take a relaxing swim at Henry David Thoreau’s Walden Pond. Get an afternoon pick-me-up at Bedford Farms for a cup of the local ice cream. Then, keep heading south to Rhode Island.
Day 4 – Providence & Newport
The smallest state’s capital, Providence, is also one of the oldest cities in the United States. However, with its commercial center, Providence Place Mall, and a large population you may not notice. Just steps from Omni Providence Hotel. Check out the city’s sites like the Rhode Island State House, Brown University and the historical Federal Hill neighborhood. Then, head down to the glamorous coastal city, Newport. Tour the Vanderbilt’s family mansion, The Breakers, and 10 other summer “cottages” that depict Newport County’s architectural heritage. You can enjoy the jaw-dropping estates and the picturesque ocean from the 3.5-mile long Cliff Walk trail. Or, check out Hammersmith Farm, the childhood home of Jacqueline Bouvier, and the site of her wedding to John F. Kennedy in 1953.
Day 5 – Cape Cod
If you’ve got time on your New England road trip, drive along the coast to Massachusetts’s famous Cape Cod peninsula. Explore Chatham’s downtown shops and restaurants, relax on Wellfleet’s White Crest Beach. With an extra day or two, extend your stay with a visit to Nantucket by ferry. Here you can stroll through the historic cobblestone streets downtown, rent bikes for a pleasurable ride to Surfside or Jetties Beach, and enjoy a fresh seafood dinner.
Summer is a great time to take a New England road trip while the weather is great. If you’re a history buff, a fan of the great outdoors or looking for charming towns, this itinerary has it all.