• Walking on Provincetown Wharf, Massachusetts
    Walking on Provincetown Wharf
    Cape Cod, Massachusetts

City Breaks

Boston is New England’s gateway city, but each New England state offers its own unique city break. The New England cities profiled below are all ideal for a weekend getaway for fun, shopping, great food, and relaxation.

New Haven, Connecticut

New Haven CT steeple

Thanks to 300-year-old Yale University, New Haven is perfect for a New England getaway. On a student-led tour, hear about former students, from actress Jodie Foster to U.S. presidents. Explore two world-class museums: Yale University Art Gallery and the Yale Center for British Art, the largest collection of British works outside Britain. Eat at excellent restaurants; relax in cheerful pubs. This New England city has a major claim to foodie fame: Louis Lunch was the birthplace of the hamburger sandwich in 1900; pizza has been served at Pepe’s since 1925.

  • Catch a play at the Yale Repertory Theatre
  • See the Beinecke Library’s rare 1455 Gutenberg Bible
  • Photograph the Amistad Memorial, a highlight of the Connecticut Freedom Trail
  • Come in June for the two-week International Festival of Arts & Ideas: a stimulating mix of music, dance, theater and more. Most events are free.

Getting there from Boston: Catch Amtrak’s Northeaster train. For travel by bus, Megabus, Peter Pan and Greyhound go to New Haven. Both buses and trains end at Union Station. Weekdays there is a free shuttle bus (bright green) to the New Haven Green.

Portland, Maine

Portland Observatory with Nautical Flags

Looking over Casco Bay and its islands, Portland is one of New England’s most popular city break destinations. Its waterfront hums with restaurants, art galleries, one-of-a-kind shops and bars with live music. Tour the Wadsworth-Longfellow House, home of poet Henry Wadsworth Longfellow; in the Portland Museum of Art, find artists inspired by Maine, such as Winslow Homer and Andrew Wyeth. And, Portland is one of the top New England cities for its restaurant and craft beer scene. Dine on contemporary dishes featuring fresh seafood. Tour one of the city's many microbreweries or take a brew tour on the Maine Brew Bus.

  • Meet artists on the monthly First Friday Art Walk; galleries and studios stay open late
  • Hear about Portland’s pirates and witches on a Wicked Walking Tour
  • Enjoy baseball the way it used to be at the Portland Sea Dogs
  • Go on a lobster boat cruise
  • Visit in October for Harvest on the Harbor — the city’s premier food and wine event

Getting there from Boston: A two-hour drive north of Boston. By train: the Amtrak Downeaster train operates five daily round trips from North Station (2-1/2 hours). By bus: Concord Coach Lines serves points in New Hampshire and Maine to Boston South Station and Logan Airport. By air: the Portland International Jetport offers daily service through several major carriers.

Portsmouth, New Hampshire

Fishing Boats

Past and present merge in this seaport, fast becoming a favorite for a New England city break. Get the lowdown at the new Discover Portsmouth Center; visit the John Paul Jones House (1758) where the “Father of the American Navy” lived. Walk the Portsmouth Harbour Trail, taking in historic homes, Market Square and Prescott Park; enjoy a harbor cruise. The story of four centuries of everyday life in America’s third-oldest city is told at Strawbery Banke Museum. Named after the first settlement, this site features historic houses furnished with antiques and everyday artifacts. Chat with costumed interpreters who cook, make barrels, garden and more.

  • Cruise the nine mysterious Isles of Shoals on a boat tour
  • Catch top-notch performances at the Music Hall and the Seacoast Repertory Theatre
  • Tour the Redhook Brewery
  • Enjoy the Prescott Park Arts Festival — a summer-long jamboree of free music, art, theatre, and dance on the banks of the Piscataqua River

Getting there from Boston: A little over an hour’s drive north of Boston. By bus: C & J Trailways offers regularly scheduled motorcoach service from Boston’s Logan Airport and the South Station train stop in Boston to Portsmouth. Upon arrival at C&J’s Portsmouth station, COAST trolley service is available to take visitors to downtown stops, year-round at select times. Limousine and taxi services are also available for the five-minute ride to downtown.

Providence, Rhode Island

Providence city skyline

One of America’s leading travel destinations, the state capital offers all the ingredients for a city getaway: riverside walks and art galleries, plus Providence Place Mall, a shopping and entertainment complex. The vibes are provided by students at Brown University and the Rhode Island School of Design (RISD). Take an audio tour as you stroll past 18th- and 19th-century homes on Benefit Street, nicknamed “the Mile of History.” This New England city was consistently voted in the top five food cities in the USA by Travel & Leisure magazine: you’ll find many Italian restaurants on Federal Hill, and modern American downtown.

  • See downtown on a romantic Venetian gondola tour
  • Watch a play at the Tony Award-winning Trinity Repertory Company
  • Bike the 14.5-mile East Bay Bike Path along Narragansett Bay to Bristol
  • Don’t miss WaterFire: Providence’s signature event from May–October, with a series of 100 bonfires blazing on the city’s three rivers and music from around the world

Getting there from Boston: An hour’s drive south of Boston. By train: Amtrak leaves from Boston’s South Station with a 35-45 minute ride. The T.F. Green airport is ten minutes from the city.