Boston is within a weekend of three states' coastlines, the White Mountains and the Green, the Berkshires, and two more cities down the line. The question is the drive: Manhattan four hours south eats most of a Friday and a Sunday in the car, so it is the drive time, not the map distance, that decides whether a place is worth two nights. Everything below is a genuine weekend trip, sorted by how far it sits from the city. 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. One of these, Provincetown, runs a fast ferry from Boston that beats the drive around the Cape.
The getaways, mapped
Every pick around Boston, numbered to match the table — with the drive and cost.
The short list
| Destination | When to go | Interests | |||
|---|---|---|---|---|---|
| Lincoln | ~50m · 46 mi | White Mountains | $610–840 | October | |
| Gloucester | ~50m · 40 mi | Cape Ann coast | $600–830 | July | |
| Portsmouth | ~1h 10m · 57 mi | Seacoast town | $610–840 | June | |
| Newport | ~1h 30m · 71 mi | Gilded Age mansions | $620–840 | June | |
| Kennebunkport | ~1h 40m · 85 mi | Maine coast | $620–850 | August | |
| Northampton | ~1h 40m · 105 mi | Valley college town | $620–850 | September | |
| Stockbridge | ~2h 10m · 130 mi | The Berkshires | $640–870 | October | |
| Provincetown | ~2h 10m · 115 mi | Cape Cod tip | $610–840 | June | |
| Stowe | ~3h 10m · 199 mi | Vermont mountains | $660–890 | October | |
| Burlington | ~3h 20m · 217 mi | Lake Champlain | $660–890 | July | |
| New York City | ~3h 50m · 214 mi | The big city | $660–900 | October | |
| Cooperstown | ~3h 50m · 240 mi | Baseball Hall of Fame | $670–900 | July |
The drive column is the one that matters for a weekend. Under an hour to Gloucester or the White Mountains leaves nearly the whole weekend; the four-hour runs to New York and Cooperstown are a real Friday haul. Costs stay in a tight band across New England.
Best for the coast
New England's shoreline is the region's summer draw, and four towns work it.
Gloucester
Fifty minutes north on Cape Ann, Gloucester is the closest coastal escape and the working-harbor one. America's oldest fishing port keeps a fleet and a memorial to the men lost at sea, the Rocky Neck art colony fills the harbor with studios, and Good Harbor Beach handles the swimming. July, for warm water and the whale-watching season offshore.
Gloucester
Portsmouth
An hour and ten north, Portsmouth is the seacoast-town weekend. New Hampshire's brief stretch of coast centers on a walkable colonial downtown, the Strawbery Banke living-history museum runs costumed streets, and the harbor packs a restaurant scene above its weight. June, for warm days before the peak-summer crowds.
Portsmouth
Kennebunkport
An hour and forty up the Maine coast, Kennebunkport is the lobster-shack weekend. Goose Rocks Beach runs wide and calm, Dock Square fills with shops, and the roadside stands do the lobster roll the state is known for. August, for the warmest water and full summer sun.
Kennebunkport
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 the fishing harbor, the dunes and the National Seashore beaches run behind town, and the arts and nightlife scene is among the liveliest on the coast. The fast ferry from Boston beats the drive around the Cape. June, for warm days before the July crush.
Provincetown
Best for the mountains and lakes
North of the city, the coast gives way to the White and Green Mountains.
Lincoln
Fifty minutes north, Lincoln is the White Mountains weekend and the closest mountain one. It sits at the western end of the Kancamagus Highway, one of the best fall-foliage drives in the country, with Franconia Notch and its cliffs and flumes a short way north. October, for peak color on the pass, though it draws the crowds it deserves.
Lincoln
Stowe
Three hours and ten into Vermont, Stowe is the Green Mountains weekend. Mount Mansfield rises above the village, the toll road and gondola climb it in summer, and the waterfalls and covered bridges fill the valley. October, for the foliage, or winter for the skiing.
Stowe
Burlington
Three hours and twenty northwest, Burlington is the lake-city weekend. Lake Champlain sets up long sunsets over the Adirondacks, the pedestrian Church Street Marketplace anchors downtown, and the waterfront runs a bike path and ferry docks. July, for warm lake days and the full summer scene.
Burlington
Best for the Berkshires and the valley
Western Massachusetts trades the coast for hills and college towns.
Stockbridge
Two hours and ten west, Stockbridge is the Berkshires weekend and the Norman Rockwell one. His museum sits on the edge of town with the largest collection of his originals, and the Main Street he painted still looks the part, with Tanglewood a short drive north. October, for the foliage over the hills.
Stockbridge
Northampton
An hour and forty west, Northampton is the college-town weekend in the Pioneer Valley. Smith College anchors it, the walkable downtown runs to galleries, bookstores, and a strong music scene, and the valley towns spread out around it. September, for crisp days and the start of the academic year's energy.
Northampton
Best for a bigger trip
Three farther weekends that reward the longer drive.
Newport
An hour and thirty south, Newport is the Gilded Age weekend. The Cliff Walk threads between the Atlantic and the backs of the Vanderbilt mansions, the harbor still fills with sailboats, and the colonial center predates the mansions by a century. June, before the summer regatta crowds arrive.
Newport
New York City
Three hours and fifty south, New York is the far-city weekend and worth the haul. Broadway, the museums, and the neighborhoods take more than a weekend, but the train makes the same-city version genuinely doable if you skip the drive. October, for crisp walking weather.
New York City
Cooperstown
Three hours and fifty west, Cooperstown is the baseball weekend on Otsego Lake. The National Baseball Hall of Fame is the draw, but the lakeside village and the Glimmerglass opera fill a summer weekend beyond it. July, for the induction-week buzz and the lake at its warmest.
Cooperstown
Getting there and getting around
Boston covers more of this list by rail than most cities. The Amtrak Downeaster runs north to Portsmouth and the Maine coast, and the Northeast Regional and Acela run south to New York, so those work car-free with planning. Provincetown has a fast passenger ferry from Boston that beats the summer drive around the Cape. The White Mountains, the Berkshires, Stowe, and Burlington 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? The White Mountains at Lincoln for the Kancamagus drive at under an hour, Portsmouth for the New Hampshire seacoast, or Provincetown at the tip of Cape Cod. All are comfortable two-night trips, and P-town has a fast ferry from Boston.
What's the closest weekend getaway from Boston? Gloucester on Cape Ann and Lincoln in the White Mountains, both about 50 minutes out, one for the fishing harbor and beaches, the other for the mountain drives. Both leave nearly the whole weekend for the place itself.
What's a good coastal weekend getaway from Boston? Gloucester for Cape Ann, Portsmouth for the New Hampshire seacoast, Kennebunkport for the southern Maine coast and lobster shacks, or Provincetown at the very tip of Cape Cod. All sit under two and a half hours out.
Where can you go from Boston for a weekend without a car? The Amtrak Downeaster reaches Portsmouth 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? The White Mountains at Lincoln for the Kancamagus, Stowe in Vermont for Mount Mansfield, and the Berkshires at Stockbridge all peak for color in early-to-mid October, under three and a half hours out.
How much does a weekend getaway from Boston cost? Most of these run $600 to $900 all-in for two over two nights, covering lodging, driving, and meals. The close coast and mountain towns sit at the lower end; New York and the Vermont trips 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, the Maine coast, the White Mountains, or the run down to New York all reward the haul. Short on time, Gloucester, Lincoln, 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 in August 2026; confirm seasonal hours, ferry crossings, and transit schedules before you travel.
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NamrataPhotos from Wikimedia Commons, used under Creative Commons licenses