Best Weekend Getaways From Boston (Road Trip Distance!)

We’ve loved every visit to Boston in our travels, but quickly found that the Massachusetts city was an excellent base for trips elsewhere in the region.

I’ve already shared all of our favorite day trips from Boston, including visits to luxe Newport, Rhode Island, and all of the incredible historical sites in the region.

The weekend getaways from Boston in this guide are all deserving of more of your time, whether they’re too far for a day trip or they just have that much to offer.

I listed them all by distance and drive time, as I’m assuming road trips from Boston here. Drive time can vary widely in New England, but generally, avoiding rush hour in and around the region’s bigger cities is a great idea for a quick getaway.

Quick Tips for Your Boston Visit

Your Flight: Deals to Boston Logan International Airport are fairly easy to come by, especially if you’re flexible with your travel. Use Skyscanner to make that happen. Love deals? Subscribe to Going.

Your Accommodations: Browse Booking.com or Hotels.com for your options at all of these weekend destinations from Boston. Vrbo is my Airbnb alternative.

Your Ride: Trains and buses are available to larger cities like New York and Portland, Maine. A car will make many of these Boston road trips more efficient. Book a rental car ahead of time.

Top Spots: See Salem at Halloween, visit the fall colors in Stowe, and catch a Broadway show in New York City.

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Provincetown, Massachusetts

Distance: 116 miles
Drive Time: 2 hours 50 minutes driving; 90-minute ferry

A man poses with his dog in Provincetown.

If you leave at an off-time, you may be able to get up to this jewel of Cape Cod in about two hours and 30 minutes. More than likely, you’re not driving at the crack of dawn, so expect the trip to take about three hours unless you take the ferry.

Note: Ferries will get you to Provincetown from Boston in just 90 minutes, but they vary in frequency outside of the summer months. If you visit in the fall as we did, you’re limited to just two daily ferries.

I included towns like Hyannis along the southern end of the Cape in my guide to day trips from Boston, but this part of the state is really best with a full weekend.

You won’t have to worry about traffic back and forth from the city or catching the right ferry, and you’ll get to see some of best sunsets in Massachusetts.

Provincetown itself is a charmer with lovely beaches, cafes made for lingering, and three miles of art galleries.

Waterbury Village Historic Village, Vermont

Distance: 190 miles
Drive Time: 3 hours 10 minutes

An ice cream graveyard with silly sayings on the graves

If you’re visiting Vermont in the fall months, you likely already have the Waterbury Village Historic District in your plans. If the weather holds up, you’ll also want to include a visit to Ben & Jerry’s in that Vermont itinerary.

Waterbury is the only place in the country where you can take a factory tour of the ice cream giant. At the very least, have a chuckle at the ice cream graveyard and mourn flavors that are no longer with us.

Stowe, Vermont

Distance: 199 miles
Drive Time: 3 hours 10 minutes

Stowe is what all of your leaf-peeping dreams are made of and my favorite spot for fresh air in the fall. The colors in this place during those magical few weeks in autumn are more vibrant than anywhere else I’ve ever been.

No matter when you visit, though, don’t miss out on The Alchemist Brewery, a brewery known for one of the best beers on the planet: Heady Topper.

Fun fact: I don’t even like IPAs but there was something about this one that hit just right. You have to drink it out of the can, too.

Interested in learning more about my favorite town in Vermont as you plan a trip from Boston to Stowe? I have a guide to all of my favorite Stowe stops.

Montpelier, Vermont

Distance: 180 miles
Drive Time: 3 hours 20 minutes

No, Burlington is not the capital city of Vermont. (I just have to put that out there as some of my peers failed to Google that one.) It’s Montpelier.

You know I’m right because you’re looking at a pic I took of the Vermont State House above. That golden dome really is that vibrant, by the way.

If you’re traveling with a pup, don’t miss out on The Quirky Pet, a pet shop that’s home to several mops masquerading as dogs. You’ll know ’em when you see ’em.

Rockland, Maine

Distance: 189 miles
Drive Time: 3 hours 25 minutes

Picturesque Rockland is one of my favorite towns in Maine and it’s popular with locals, too. The lighthouse action alone here is worth the weekend trip from Boston.

See the Rockland Breakwater Lighthouse and the nearby Owls Head Lighthouse and you’ll treat yourself to two of the most photogenic lighthouses in the state.

Note: Owls Head and Owls Head State Park are technically just outside of Rockland, but it’s a 10-minute drive if you want to make it happen.

Rockland is also known for its lobster fishing industry, so if for whatever reason you’ve yet to eat a lobster roll, this is a legit place to do so.

Bangor, Maine

Distance: 240 miles
Drive Time: 3 hours 25 minutes

We made the trip to Bangor for one reason and one reason only: the Stephen King house.

It’s no longer technically the Stephen King house — the author is now splitting his time between another home in Maine and Florida — but you’ll still find fans waiting outside.

Fun fact: On our visit in October, there was a red balloon tied to the spooky front gate in honor of that one clown he created. You know the one.

The folks who will be running the writer’s retreat at the property today will likely keep up the tradition for other tourists who want to visit the Victorian mansion.

The place has wrought iron bats decorating the front gate, for Pete’s sake. It’s an excellent piece of local history.

New York City, New York

Distance: 215 miles
Drive Time: 4 hours 10 minutes

Two women pose on Broadway in New York City.

New York City begs for as much time as you’re willing to give it. I could spend a full day just eating all of the quintessential New York foods and not even touch any of the cultural attractions.

If you’re able, snag some tickets to a Broadway show while you’re there. You don’t have to drop the first and last month’s rent to make that happen, either.

Line up at the box office for same-day tickets if you’re of the patient sort or browse sites like TodayTix for rush tickets and day-of deals.

You can even take advantage of same-day resale tickets from desperate patrons of the arts. There are ways to make it happen, especially if you’re not trying to get in on the hottest ticket in town.

Acadia National Park, Maine

Distance: 280 miles
Drive Time: 4 hours 30 minutes

A woman poses at the top of a summit in Acadia National Park.

Acadia is one the most beautiful national parks in the country, but it can be challenging to get to if you’re not already on the East Coast. If you have the time, make use of your proximity to Boston and visit Acadia.

Otherwise, don’t miss out on the park’s best hikes and sites, like the Ocean Path Trail, Cadillac Mountain, and Acadia’s unique carriage roads. This is a place that begs for more of your time.

Bar Harbor, Maine

Distance: 285 miles
Drive Time: 4 hours 40 minutes

A woman poses with her dog on a hike in Acadia National Park.

Bar Harbor is a natural base for travel into Acadia National Park, but book well ahead of your trip if you’re visiting in the summer and fall months. The town is expensive thanks to its proximity.

Once you’re done at the park, there’s plenty to occupy your time in Bar Harbor proper. Walk the lovely Bar Harbor Shore Path, fish for Maine lobster, and visit Bar Island.

Downtown Bar Harbor is worth your time, too. Charming Main Street is home to the town’s best restaurants and boutique shopping.

More of the Best Weekend Trips from Boston

I’ve seen a lot, but there’s so much more to see as far as overnight trips from Boston and long weekends.

Check out some of the Boston weekend trips that top my list for future trips, including the fancy ones that just haven’t been in the budget just yet:

Nantucket (2 hours 30 minutes+): Some of these lists say you can do this trip in a day, but I really don’t recommend it. This is one of the best Boston day trips by ferry, which is why I added that little + for emphasis.
Stockbridge (2 hours 35 minutes): Stockbridge is doable on a long day trip from Boston, but the Berkshires as a whole are really best experienced on a weekend away.
White Mountain National Forest (2 hours 40 minutes): The White Mountains span New Hampshire and Maine, although most of the best leaf peeping is supposedly in New Hampshire. You’ll want to stay a while once you’re there.
Martha’s Vineyard (3 hours+): Much like Nantucket, your travel time for Martha’s Vineyard will depend on the ferries available when you take your trip. It’s much better to plan for a full weekend to get a feel for how the fancy set lives.
Block Island, Rhode Island (3 hours+): Time varies on this one as there’s a ferry involved. Once you’re there, expect scenic beaches, dramatic cliffs, and several historic lighthouses to admire.
Burlington, Vermont (4 hours 15 minutes): We never made it to the state’s largest city despite lots of Vermont travel. It’s firmly at the top of our list for the scenery alone, nestled all cute between the Adirondack Mountains and Lake Champlain.

Boston is an excellent base for travel.

Boston itself is a pretty fun trip, too, especially if you’re at all into American history.

If you’re lucky enough to be here in the summer and fall, it’s a great spot to start for short trips from Boston. This is when the region comes alive.

I’m sure we’ll be back if only to tick off the White Mountains, which look like one of the most scenic places to visit near Boston. We just didn’t plan ahead far enough for that one on our last autumn adventure in New England.

When the mountains are calling, you must answer!

Lingering on the East Coast? Check these out:

These American cities are pretty great, too:

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