Boston to Northeast Road Trip Tritinerary

Nothing compares to the buzz of live baseball, America’s favorite pastime, at arguably the most famous ballpark in the US, Fenway Park. Book a stadium tour or pre-game tour to get in some batting practice at the aptly named Green Monster, or better yet, go watch a game and experience the historic grounds of the oldest Major League Baseball stadium–home of the Boston Red Sox. Book early as games almost always sell out. A hotdog before you enter the stadium is a local pre-game tradition. The Sausage Guy is perhaps the most well-known and loved Fenway Park food cart.

One of the most walkable cities in the USA, activity-based adventure can be discovered on foot or bike around nearly every corner of Boston. The Boston Harborwalk offers waterfront walking paths that wind around the city. Or take a city bike to one of two Paddle Boston locations along the Charles River where you can rent kayaks, canoes and paddle boards for a day on the water. Tours and guided trips are also available.

Any trip to the Northeast is made better with a detour to see Manhattan’s iconic sites. The Statue of Liberty in New York Harbor is a landmark that’s also steeped in history and symbolism. If you want to climb to the Pedestal or Crown, tickets must be booked in advance with Statue City Cruises, the only official ticket seller. There are other operators who offer some combination of ferry transport, guided tours of Liberty Island and entry to the Statue of Liberty Museum–it’s advisable to check the inclusions and book in advance.

The two observation decks at the legendary Empire State Building are four miles away in Midtown. If you have time and comfortable shoes, make the 90-minute journey from Battery Park on foot and take in the celebrated Washington Square Park and Flatiron building en route. Detour to the Soho streets west of Broadway for some of the city’s best boutique shopping.

Midtown is home to some of Manhattan’s most famous hotels. The Waldorf Astoria’s long-awaited reopening is scheduled for Spring 2025 (it closed in 2017 for extensive renovations), while a short walk up Madison Avenue is another notable hotel, The St. Regis. For a classic Midtown food experience, the Gramercy Tavern is synonymous with New York bistro dining and recently celebrated its 30-year anniversary.

The Hotel Chelsea has a storied history thanks to the coterie of literary, arts and music figures who called it home during the sixties and seventies. These days it’s a comfortable and stylish 4.5-star hotel. La Esquina has become a legendary Manhattan experience thanks to its beginning in 2006 as an underground restaurant with no visible door and scarce bookings. These days there are five locations, including midtown. Visit for tacos regularly awarded New York’s best.

One of the most-visited National Parks in the US is driving distance from Boston—an opportunity for nature lovers that’s too good to miss. Acadia is celebrated for its diverse natural beauty (a captivating mix of forest, coastline and mountains) and outstanding wildlife. A trip to the park may involve an encounter with seals, bobcats, foxes, deer or beavers, while the park’s 300 avian species makes its bird watching some of the finest in the US.

Located largely on Mount Desert Island (accessible by bridge), entrance passes are required year round, while visitors between May and October require a pre-booked reservation for Cadillac Mountain, famed for its views. Book well in advance to secure a coveted sunrise or sunset spot. Bass Harbor Lighthouse (pictured) is on the southernmost tip of the island. Walking boots are advised if you intend to access the rocky vantage points.

Accommodation options, including campsites, are dotted around Mount Desert Island but Bar Harbor is the most popular area. Hotels range from good-value 3-star chains to quaint bed and breakfasts, such as Bass Cottage Inn.

Drive to Maine just for a lobster roll? Well yes, actually. You’ll come for the rolls but stay for delightful seaside towns and cities, such as Portland, less than two hours’ drive from Boston. Maine is the lobster capital of the USA and is famed for its hot-buttered buns filled with the freshest lobster you’re ever likely to eat. Eventide or Bite Into Maine are two Portland eateries routinely recommended for their standout rolls.

Portland is fast forging a reputation for its dynamic food scene. ZU Bakery and Norimoto Bakery both won prestigious James Beard food awards. Norimoto’s promise of “European baking, Japanese sensibility and Maine ingredients” is led by baker Atsuko Fujimoto, who moved to Portland from Tokyo in 2002. The epicenter of the city’s food scene is Washington Avenue, where you can find Texas-style barbecue, Japanese, Vietnamese, and Salvadorian cuisine, among others.

With more than 20 craft breweries in the area, Portland’s drinks game is as strong as the food. To sample a local drop, head to Industrial Way in the Riverton area, home to six different breweries, including the celebrated Allagash Brewing Company. The East Bayside area is another craft beer hotspot, here you’ll find Austin Street Brewery and Rising Tide.

When you’ve had your fill, Portland Harbor Hotel is located in the Old Port area, walking distance to Washington Avenue eateries and Commercial Street, the picturesque main street.

Less than two hours’ drive south of Boston, the seaside idyll of Newport has an abundance of fancy houses and a long history as a summer destination for wealthy New Yorkers. Thanks to The Preservation Society of Newport, a not-for-profit cultural organization that turns historic mansions into museums, you can visit 11 different luxurious houses in the Newport area.

These include Kingscote, which fans of the HBO series Gilded Age will recognize as a location from season two. The grandest and most famous of all is The Breakers, built by the Vanderbilts, arguably the wealthiest and best known Gilded Age family. With a huge cliff to itself and water views, the opulent palazzo-style mansion is now also open to the public. Newport Mansions plays host to a busy program of events throughout the year, be sure to check what’s scheduled.

Newport still has an upmarket reputation today. It’s compact and highly walkable, making it ideal for a walking tour. If you’d prefer to freestyle it, Thames Street (the main shopping and eating strip) and the seaside Cliff Walk are bound to impress, with the latter offering more mansion sightings. There’s no shortage of swanky places to stay in Newport. Built in 2023, Gardiner House is one of the newest hotels in the area, and has a central waterfront location and chic interiors.

A picture-perfect residential neighborhood, Beacon Hill is ideal for slow discovery on foot. You’ll find cobblestone streets, stunning colonial architecture, quaint stores and two major cultural stops: the Massachusetts State House and the Museum of African American History.

In 2024, Architectural Digest crowned the area’s Acorn Street, one of the most beautiful streets in the world, making it especially photogenic, but also guaranteeing crowds. Charles Street is the area’s pretty main thoroughfare, wander along and shop the independent boutiques selling fashion, art and antiques. Beacon Hill Books & Cafe is made for leisurely browsing.

For a serene outdoor experience in Beacon Hill, try a small-group walking tour or head to the Charles River Esplanade for green space, outdoor activities and a kids’ playground. Make a pit-stop for deli-style sandwiches at Flour Bakery or DeLuca’s Market before finishing your picnic with a sweet selection from Beacon Hill Chocolates.

The refined Beacon Hill Hotel is located between Boston Common and the river. It’s a peaceful retreat from the city buzz and the ideal base from which to explore Beacon Hill at your leisure.