7 Spectacular Weekend Road Trips from Boston, Massachusetts

Posted by
Sarah Lamagna
May 25, 2021
Updated April 11, 2023

weekend road trips from boston ma
Photo: Colin D. Young / Shutterstock

Tired of the cobblestone streets and “R’s” left out of every word? Luckily for the residents of Boston, there are some epic weekend road trips within a few hours of the city.

Boston might be home to some incredible sights and truly dedicated sports fans, but sometimes a weekend away is just what the doctor ordered.

Whether you’re looking for gorgeous coastal villages, quaint mountain towns, some good ol’ fashioned Ben & Jerry’s ice cream, or views from the top of Mount Washington, we’ve got what you need.

Related Read: 10 Chill Romantic Getaways in Massachusetts

Road Trip Planning

Before you head out, make sure to plan accordingly. Unlike a lot of other places across the country, weather and traffic are fairly predictable in and around Boston. There usually aren’t “surprise” storms and traffic is, well, always there.

Expect typical weather patterns during corresponding seasons: it snows in the winter, rains in the spring and fall, and is hot/humid in the summer. You won’t need any special car enhancements (like four-wheel drive) to get to any of the places on this list. But beware of potholes – they are a’plenty in the northeast. Construction crews never seem to be able to keep up with them.

Speaking of construction; it’s constant in New England and especially in Boston. Construction crews are out in freezing temperatures and rainy days. Expect traffic to be slower and heavier in these areas. It’s also important to note that depending on your destination from Boston, you might pass through several rush hours.

There’s also a reason that Boston drivers are well-known across the country; they are aggressive. Come prepared knowing that if you stall too long when a red light turns green, you will definitely be beeped at – car horns are the state bird call of Massachusetts…just kidding.

Pro tip: do NOT dilly dally in the passing lane. This is a huge pet peeve of most New Englanders. If you aren’t passing someone, get out of that lane.

Related Read: 5 Best Day Trips From Boston for Scenic New England Getaways

7 Amazing Weekend Trips from Boston

1. North Conway, NH

North Conway, NH
Photo: Nick Beer / Shutterstock

This picturesque town has everything you’ll need for outdoor adventure. North Conway is in the heart of White Mountain National Forest which prides itself in a myriad of outdoor activities including hiking, biking, skiing, and fishing (among others).

Mount Washington looms in the distance as if beckoning you to climb it. At 6,288’ above sea level, Mount Washington is the tallest mountain in the northeast. You can climb it anytime of year (although we recommend a guide service like Nemo Mountaineering in the winter) through several routes, with the Tuckerman Ravine route being the most popular. You can also drive up yourself during the late spring/summer months or take the Cog Railway.

The heights around Mount Washington aren’t for everyone, though. Instead, you can take a drive along the Kancamagus Highway (the Kanc to locals). It can get busy on the weekends, especially during peak leaf-peeping season in the autumn.

You can also simply hang around town: visit Zeb’s General Store, grab brunch at Peach’s Restaurant, drink a beer at Moat Mountain Smokehouse and Brewing, or visit the Conway Scenic Railroad.

  • Distance from Boston: 137 miles
  • Drive time: 2 hours, 30 minutes

2. Westerly, RI

ocean house westerly rhode island
Photo: Allard One / Shutterstock

Head on down to this southern Rhode Island beach town to catch some waves and rays (and maybe a glimpse of TSwift). It’s the shortest trip on our list from Boston which means extra time to soak in the sun and get that tan you’ve been yearning for.

The best place for getting in that vitamin D is at Watch Hill. It’s great for kids and adults alike and includes a Merry-Go-Round where kids can take their chances grabbing brass rings for a shot at a free ride – psst…make sure to grab an outside horse to do this.

Aside from beaches, there’s plenty of other things to do including popping your head into a few boutiques like Anther Living and Rochelle’s. For some good food (or a great place to stay), check out Ocean House’s many culinary journeys including a taco shack, a secret garden creperie, and a raw bar – among so much more.

  • Distance from Boston: 92 miles
  • Drive time: 1 hour, 30 minutes

3. North Adams, MA

north adams road trip
Photo: Joseph Sohm / Shutterstock

Grab a wand and your spell book to head to the place that inspired writers like J.K. Rowling, Henry David Thoreau, and Herman Melville. Located in northwestern Massachusetts, North Adams is in the heart of the Berkshire Mountains.

You can head up to the top of the state to visit Mount Greylock and the Massachusetts War Memorial Tower. On a clear day, you can see for 70 miles in either direction into five states.

Too bad you didn’t really know magic, though, and get yourself back down to town quickly. Whenever you do, head over to PUBLIC for some great eats and then to Bright Ideas Brewing for the best brewery in town.

  • Distance from Boston: 136 miles
  • Drive time: 2 hours, 45 minutes

Related Read: 10 of the Best Airbnbs in Boston, Massachusetts

4. Lake George, NY

sagamore hotel lake george ny
Photo: Shutterstock

If you’re in the mood for some lake-living, then Lake George is your answer. It’s full of every type of water-related activity you can think of: boating, kayaking, water skiing, canoeing, fishing, and even hopping on a cruise. But if water isn’t your thing, well, maybe go elsewhere?

Seriously, though, on top of every water sport in the world, Lake George has many land activities. For the most unique experience on land, though, consider taking a rail bike tour through the Adirondacks. Or you could check out the Natural Stone Bridge and Caves, which is home to the largest marble cave entrance in the eastern United States.

  • Distance from Boston: 227 miles
  • Drive time: 3 hours, 30 minutes

5. Mystic, CT

mystic ct road trip
Photo: Faina Gurevich / Shutterstock

Move over Leonardo Dicaprio, Mystic is the true home of the hero of the Titanic. That is, Bob Ballard who discovered the famous ship wreckage. He founded the Institute for Exploration which partnered with the Mystic Aquarium – located in, you guessed it, Mystic.

But this quaint, coastal town is more than marine ecosystems. You can travel back in time and visit Mystic Seaport Village and set foot on a veteran training ship. If you need to pick up some trinkets for your family or friends, head to Franklin’s General Store in Olde Mystick Village. Grab a pizza slice from famed Mystic Pizza (yup, it’s the same one in the movie starring Julia Roberts). To wind down for the evening, get a scoop of ice cream from Mystic Drawbridge Ice Cream and watch the boats head down the Mystic River.

  • Distance from Boston: 100 miles
  • Drive time: 1 hour, 40 minutes

Related Read: The 6 Best Scenic Byways to Fully Experience Massachusetts

6. Stowe, VT

Stowe, VT
Photo: Songquan Deng / Shutterstock

No matter the time of year you visit this northern Vermont town, Stowe is perfect for any traveler. Into skiing? Head to Stowe Mountain Resort. Rather have a spa day? Then Stoweflake is your destination. Or maybe you just want some ice cream? Then take a tour of the hippie owners’ flagship Ben & Jerry’s store in Waterbury (just south of Stowe).

A trip to Stowe isn’t a trip, though, until you visit the Trapp Family Lodge. You can stay there the entire weekend, grab a beer from the von Trapp Brewery, or experience one of the many activities there including disc golf, biking, hiking, and carriage rides.

Pro tip: don your best dirndl or lederhosen during their Oktoberfest. It’s a heck of a time!

  • Distance from Boston: 199 miles
  • Drive time: 3 hours

7. Kennebunkport, ME

Kennebunkport maine weekend trip
Photo: Shutterstock

Kennebunkport is THE quintessential New England coastal town. To get a real feel for its personality, head on out to Dock Square where you can peruse art and buy some fashionable clothing at the boutique shops or sit in one of the many cafes along the main drag.

Get your lobster fix at Port Lobster or Mabel’s (they’re both favorites for the locals) or try the famed Whoopie Pie found at HB Provisions. For adventurous souls, visit the Rachel Carson National Wildlife Refuge or kayak around Cape Porpoise Pier. End your day by resting your head (or simply walking around the 60 acres of lush gardens) at St. Anthony’s Monastery and Franciscan Guest House.

  • Distance from Denver: 84 miles
  • Drive time: 1 hour, 30 minutes

Explore New England

Sign up for Weekend Wanderer to join thousands of readers getting epic travel ideas every week!

Seen in: Massachusetts, New England, Road Trips

Find your next adventure

Sign up for Weekend Wanderer and join thousands of readers getting epic travel ideas weekly.

Related Posts

arizona new mexico road trip

Arizona to New Mexico Road Trips: 25 Scenic Side Trips

“People who live in Arizona have easy access to some of the most extraordinary landscapes on the entire planet,” says Rick Quinn, “and I’m continually amazed by how few Arizonans take advantage of more than a tiny fraction of their options.” Rick is the author of the new book Arizona and New Mexico: 25 Scenic Side Trips, a guide to road trips that start and end at Interstate highways but take travelers into the heart of what makes the Southwest so captivating.