Weekend Getaways From Boston: Drive Times & Cost

From Cape Ann to Acadia, Boston's weekend map is a shoreline. Most of what deserves two nights from this city touches salt water, and the list below leans into that. It now runs twenty-one deep, from a 50-minute Cape Ann run to a Victorian beach town nearly six hours south, sorted by how far each sits from the city, because it is the drive time, not the map distance, that decides whether a place is worth a weekend. Verified drive times, an honest all-in cost for two, and the month worth going.

Every drive time here was checked against a routing source, not the optimistic figure, and labeled one-way in typical traffic. The cost is an honest all-in estimate for two over two nights: lodging, driving, and meals out. Two of these bring a boat into it: Provincetown runs a summer fast ferry from Boston that beats the drive around the Cape, and Greenport pairs the drive to New London with the Cross Sound Ferry.

The short list#

The drive column is the one that matters for a weekend. Eight of these sit within two hours and leave nearly the whole weekend for the place itself; the near-six-hour runs to Cape May and Alexandria Bay are a real Friday haul. Costs hold a tight band, $600 to $940 for two.

Best for the Maine coast#

If you make one coastal weekend from Boston, make it Portland. Kennebunkport is the shorter version, Bar Harbor the far one.

Portland#

An hour and fifty up I-95, Portland is the anchor of the Maine coast. The Old Port district is walkable end to end and does the fresh-seafood weekend at a stroller's pace, while the Maine Narrow Gauge Railroad museum keeps its historic trains running along the Casco Bay waterfront. September, after the summer rush.

Portland

Kennebunkport#

An hour and forty up the coast, Kennebunkport is the compact version of the Maine shore. Goose Rocks Beach runs wide, with coastal walking paths along the Atlantic, Dock Square packs the boutiques and galleries into the harbor district, and Walker Point sits on the shore drive out of town. June, before the deep-summer crowds.

Kennebunkport

Bar Harbor#

Four hours and forty north, Bar Harbor is the far end of the Maine coast argument and the reason to stretch a weekend. Acadia National Park starts at the edge of town: Thunder Hole booms where the Atlantic slams the granite, the trails climb to sunrise views from the highest point on the Atlantic coast, and the Shore Path and the whale-watch boats cover the in-town hours. July, in the full swing of the season.

Bar Harbor

Best for the New England coast#

The nearer water runs from a 50-minute harbor to a wine-country fork across a ferry, with one far-south outlier tacked on.

Gloucester#

Fifty minutes north on Cape Ann, Gloucester is the shortest overnight on the list. Cape Ann harbor tours run out among the fishing fleet and the marine wildlife of a historic port that still fishes, the Rocky Neck Art Colony paints it, and Good Harbor Beach handles the swimming. August, at the height of beach weather.

Gloucester

Provincetown#

Two hours and ten to the very tip of Cape Cod, Provincetown is the end-of-the-land weekend. The Pilgrim Monument towers over a harbor of colorful trawlers, Commercial Street carries the arts scene, and the National Seashore beaches and the Dolphin Fleet whale watch fill the days. The summer fast ferry from Boston beats the drive around the Cape. June, before the July crush.

Provincetown

Newport#

An hour and twenty south, Newport is the Gilded Age weekend. The Cliff Walk threads between the Atlantic and the backs of the mansions, The Breakers is the one to tour, and the harbor around Bowen Wharf still runs on sails. June, when the sailing season fills the water.

Newport

Mystic#

An hour and forty southwest into Connecticut, Mystic is the seaport weekend. The Seaport Museum recreates a nineteenth-century seafaring village around its historic wooden ships, the aquarium holds the other end of town, and downtown's riverfront restaurants take the evenings. July, at the height of the season.

Mystic

Greenport#

Three hours and twenty with a boat in the middle: drive to New London, and the Cross Sound Ferry carries you across to Long Island's North Fork. Greenport is the wine village at the end of it, a maritime town ringed by vineyards pouring the local whites, with Bedell Cellars the tasting stop and Orient Beach State Park closing out the fork. September, at harvest.

Greenport

Cape May#

The far edge: nearly six hours south, Cape May is the Victorian beach town at the end of New Jersey. Victorian houses line the streets behind the beachfront, the Emlen Physick Estate is the one to tour, and the lighthouse at Cape May Point State Park puts the whole Atlantic horizon on its observation deck. June, before the peak.

Cape May

Best for the mountains and foliage#

The White Mountains, the Greens, and the Berkshires stack north to west, and October is the month that matters for most of them.

North Conway#

Two and a half hours north, North Conway is the White Mountains weekend. The Conway Scenic Railroad pulls out of its historic station and into the mountain landscape, Diana's Baths' cascades sit outside town, and Cranmore Mountain Resort covers the winter version. October, when the color comes down the valley and the town fills accordingly.

North Conway

Stowe#

Three hours and ten into Vermont, Stowe is the ski-village weekend. Mount Mansfield's alpine terrain runs winter sports in season and valley hiking in summer, the resort handles the lifts, and the Gold Brook Covered Bridge is the small detour worth taking. January, when the village is at its coziest and the snow is the point.

Stowe

Manchester#

Three hours and ten west sits Manchester, Vermont, the Green Mountains town rather than the New Hampshire city. Hildene, the historic estate, keeps its preserved gardens under long mountain views, and the designer outlets absorb a rainy afternoon. October, under peak color.

Manchester

Stockbridge#

Two hours and ten west, Stockbridge is the Berkshires weekend. The Norman Rockwell Museum holds the paintings of American small-town life, and the hills around town supply the quiet walking paths that are the other half of the trip. October, for the color over the Berkshires.

Stockbridge

Northampton#

An hour and forty west, Northampton is the college-town weekend. The Smith College Museum of Art runs from historic to modern pieces, Thornes Marketplace and the Academy of Music Theatre hold down the walkable center, and the Norwottuck Rail Trail rolls flat out of town for a morning ride. May, when the valley turns green.

Northampton

Best for the cities#

Four city weekends, from under an hour to just under four.

Providence#

Fifty-odd minutes south, Providence is the closest city swap. On WaterFire nights, bonfire installations burn down the middle of the river through downtown, the Rhode Island School of Design Museum rewards a slow morning, and the Italian restaurants settle the question of dinner. September, with summer's crowds gone.

Providence

Portsmouth#

An hour and ten north, Portsmouth compresses four centuries into a walkable seacoast town. The Strawbery Banke Museum keeps restored homes spanning those centuries, and the cafes along the water set the pace for the rest. September, in the calm after summer.

Portsmouth

Burlington#

Three hours and twenty northwest, Burlington is the lake-city weekend. The pedestrian Church Street Marketplace runs Vermont crafts and restaurants down its middle, Waterfront Park opens onto Lake Champlain, and the Spirit of Ethan Allen cruises the sunset. September, before the cold and after the crowds.

Burlington

New York#

Three hours and fifty south, New York is the far-city weekend and worth the haul. The Metropolitan Museum and Central Park anchor the classic version, a Circle Line boat circles the skyline past the Statue of Liberty, and a show at the Majestic Theatre closes the night. The train makes it car-free, which the getting-around note covers. October, for crisp walking weather.

New York

Best for upstate New York#

Three weekends that pay back the longer drive west.

Saratoga Springs#

Three hours and ten west, Saratoga Springs is the racing weekend. The Saratoga Race Course runs its historic meet in high summer, the mineral springs bubble up through Saratoga Spa State Park, and the Performing Arts Center and the National Historical Park round out the days. August, mid-meet.

Saratoga Springs

Cooperstown#

Three hours and fifty west, Cooperstown is the baseball weekend. The National Baseball Hall of Fame documents the national pastime in a lakeside village that stays quiet around it, The Farmers Museum adds the rural-history side, and Glimmerglass State Park puts the lake within reach. July, when the village is in full season.

Cooperstown

Alexandria Bay#

Nearly six hours northwest, Alexandria Bay is the Thousand Islands weekend and the far edge in the other direction. Boldt Castle stands on Heart Island as a monument to turn-of-the-century craftsmanship, Uncle Sam Boat Tours thread the channels past mansions scattered across the river, and Wellesley Island State Park covers the swim-and-camp side. June, at the start of the boat season.

Alexandria Bay

Getting there and getting around#

A car covers all twenty-one, and a few trips improve on it. The Amtrak Downeaster runs north to Portland and the Maine coast, so the lead pick works car-free. The Northeast Regional and Acela make New York a train weekend that skips the I-95 crawl, and Provincetown runs a fast passenger ferry from Boston in summer that beats the drive around the Cape. Greenport is the hybrid: drive to New London, then ride the Cross Sound Ferry across to the North Fork. The White Mountains, the Green Mountains, and the Berkshires all need a car. Confirm current Amtrak and ferry schedules before you plan around them.

Common questions#

What's the best weekend getaway from Boston? Portland for the Maine coast at just under two hours, North Conway for the White Mountains at two and a half, or Newport for the Gilded Age mansions at under an hour and a half. Provincetown adds the Cape Cod tip, with a fast ferry from Boston in summer.

What's the closest weekend getaway from Boston? Gloucester on Cape Ann, about 50 minutes north, with the working harbor, Good Harbor Beach, and the Rocky Neck Art Colony. Providence is just under an hour south, and Portsmouth sits at about an hour and ten.

Is Portland, Maine a weekend trip from Boston? Yes, about an hour and fifty minutes up I-95, and the Amtrak Downeaster runs there car-free. The walkable Old Port district and the narrow-gauge railroad museum on the Casco Bay waterfront fill two nights, and September is the month to go.

How many weekend getaways are within 2 hours of Boston? Eight of the twenty-one sit within two hours: Gloucester at 50 minutes, then Providence, Portsmouth, Newport, Kennebunkport, Mystic, Northampton, and Portland at just under two. Stockbridge and Provincetown land a few minutes past the line.

What's a good coastal weekend getaway from Boston? Gloucester for Cape Ann at 50 minutes, Newport for the Cliff Walk and the mansions, Kennebunkport and Portland for the Maine coast, or Provincetown at the tip of Cape Cod. Cape May, the Victorian beach town nearly six hours south, is the far edge of a weekend.

Where can you go from Boston for a weekend without a car? The Amtrak Downeaster reaches Portland and the Maine coast, and the Northeast Regional and Acela run to New York. Provincetown has a fast passenger ferry from Boston in the summer. The mountains and the Berkshires need a car.

What's the best fall foliage weekend from Boston? North Conway in the White Mountains, two and a half hours up, pairs peak color with the Conway Scenic Railroad's runs into the mountain landscape. Stowe under Mount Mansfield, Manchester in Vermont, and Stockbridge in the Berkshires follow in early-to-mid October.

How much does a weekend getaway from Boston cost? Most of these run $600 to $940 all-in for two over two nights, covering lodging, driving, and meals. Gloucester, Providence, and Provincetown sit at the lower end; Cape May and Alexandria Bay, the two long hauls, at the higher.

The bottom line#

The best weekend getaway from Boston is the one whose drive leaves you time to enjoy it. With a full weekend, Portland, Bar Harbor, or the run down to New York reward the haul. Short on time, Gloucester, Providence, or Portsmouth keep you close and back by Sunday. Either way, plan your weekend free and the planner ranks these for your exact dates, group, and budget.

Browse more weekend getaways by city, or for a same-day trip see the day trips by city.

Cover photo by Ian Howard (CC BY 2.5) via Wikimedia Commons. Drive times verified against routing sources August 2026; confirm seasonal hours, ferry crossings, and transit schedules before you travel.