8 Best Road Trips in Massachusetts, USA

8th September 2021

Imagine hitting the road with your family or friends, in snack-filled car, with an awesome playlist for that long-awaited getaway. If you’re yearning for that itchy feeling of wanderlust without the hassle of having to travel abroad, look no further than the backyard of Massachusetts! From cascading waterfalls, to dreamy coastlines, and fall foliage that leaves you awe-struck, you are in for a treat that only the best road trips in Massachusetts can offer! 

This works either way if you’re taking road trips from Boston or starting anywhere on the map of Massachusetts! Spare the trouble of planning and buckle up, because we’ve compiled the eight best road trips in Massachusetts for you to choose from! 

Related read – 5 Scenic Routes for a Northeastern United States Road Trip

1 – Massachusetts Waterfall Road Trip 

Massachusetts Waterfall Road Trip

Beginning with Doane Falls as your starting point, this road trip will take you to a range of the best waterfalls The Bay State has to offer, nine of them in total! If you’re looking for day trips in Massachusetts, this sure is an exciting way to spend it, since the whole ride comes up to an all-day affair. Nothing but just wading in one waterfall after the next! Get ready to hop on one of the best road trips in Massachusetts and make some lifetime memories. 

Duration: About 8 hours drive time

Highlights: Doane Falls(Royalston); The Cascade (North Adams), Wahconah Falls (Dalton); March Cataract Falls  (Williamstown), Bash Bish Falls; Race Brook Falls (Sheffield); Umpachene Falls (New Marlborough); Campbell Falls (New Marlborough); Glendale Falls (Middlefield)

Best season: After heavy rainfall in the spring when the waterfalls are at their peak

2 – Lighthouse Road Trip in Massachusetts 

Lighthouse Road Trip in Massachusetts

If a Massachusetts Waterfall Road Trip isn’t your thing, fret not, because the picturesque coastal drives in Massachusetts are just as attractive to set your sights on. A short stop along the coastal line guarantees that sun on your skin and salt in your hair. This trip is ideal, especially if you’re on the hunt for road trips from Boston during the warmer months.

The panoramic coastal drives in Massachusetts from Crane’s Beach all the way to Cape Cod offer from great national preserved seashores for a day’s picnic, to historical lighthouse tours and more. Be sure to add the oldest American Lighthouse to your Massachusetts road trip itinerary so you don’t miss it. 

Duration: 9 Hours drive time 

Highlights: Crane’s Beach (Ipswich); Eastern Point Light, Boston Light (Little Brewster Island); Minot’s Ledge Light (Scituate); Plymouth Light, Nobska Light (Wood’s Hole); Chatham Light (Chatham); Nauset Light (Eastham); Cape Cod (Highland) 

Best season: Spring to Summer

3 – Fall Foliage Road Trip 

Fall Foliage Road Trip

To add on to the list of the best Massachusetts road trips is the home of the most breath-taking and wonderful array of fall foliage along the Mohawk Trail. If you’re looking to rest your sights on some colorful, scenic drives in Massachusetts during the fall, this is the perfect opportunity to grab! 

The list of jam-packed activities along the way, from picking your own cranberries to visiting old colonial museums could also make this perfect for taking day trips in Massachusetts. The trip starts from Appleton Farms all the way to the charming town of Deerfield and ends at the Savoy Mountain State Forest. 

Duration: About 9 hours drive time. 

Highlights: Appleton Farms(Hamilton); Wachusett Mountains (Princeton); Deerfield; Savoy Mountain State Forest 

Best Season: Fall (Mid-October) 

4 – Christmas Lights Road Trip through Massachusetts

Christmas Lights Road Trip through Massachusetts

A must have on your Massachusetts road trip itinerary during the holidays is definitely the Christmas Lights Road Trip. Gear up, because this route will leave you with the cheer and spirit of Christmas, the kind that makes you feel homesick. Sparkly lights, vintage cars, the sound of carols and smell of hot chocolate in the air all seems too enticing an offer to turn away and is certainly no place for the Grinch! 

What better way to experience the magic of Christmas than to indulge in one of the most scenic drives in Massachusetts? Hop on and make this one of your best road trips in Massachusetts. 

Duration: About 7.5 hours drive time

Highlights: Edaville Christmas Festival of Lights (South Carver); Lighting of the Green (Taunton); La Salette Festival of Lights (Attleboro); Bright Nights Forest Park (Springfield); Stockbridge Main Street; City of Lights Parade (Lowell); Zoo Lights (Stone Zoo, Stoneham) 

Best season: Mid-November to Mid-December

5 – Mount Greylock 

Mount Greylock

This wouldn’t be a complete guide on the best road trips in Massachusetts if it didn’t include Mount Greylock. If you’re looking to fit in a good work out that offers a stellar view of surrounding Berkshire landscapes, this is the trip to hop on. 

The drive up during the fall that spans across stunning fall foliage only makes this one of the best scenic road trips in Massachusetts to look forward to. Pack in those hiking shoes and you’re good to go! 

Duration: 2.5 Hours’ drive time; 5 hours if it includes hiking 

Highlights: Summit of Mount Greylock; Western Gateway Heritage State Park

Best season: Rockwell Road (home to the scenic byway) is open from mid-May to November 1. 

6 – Jacob’s Ladder Scenic Byway (Route 20)

Jacob’s Ladder Scenic Byway

If you’re a sucker for a combination of natural wonders, lush forests and rivers, cute little towns and theatre, then you’re in store for one of the best road trips in Massachusetts. Ditch the city for a while and take in the calmness of the wetlands. Make time for a good reset with some camping, hiking, cross-country skiing, and more. 

And if you’re looking for a little history lesson, a quick stroll through the town of Lee takes you through the pages of its past and gorgeous architecture. 

Duration: About 1 hour drive time

Highlights: Chester-Blandford State Forest; Jacob’s Pillow Dance Festival (Beckett); Boston Symphony Orchestra (Tanglewood); Lee Centre

Best season: Year-round 

7 – Central Hills Loop 

Central Hills Loop

Central Hills Loop sure makes the list for one of the best scenic road trips in Massachusetts. Home to the largest body of water in the state, the Quabbin reservoir, and a line of gorgeous fall foliage, this route hosts an underrated view of the most scenic places in Massachusetts with plenty of Insta-worthy backdrops! 

Duration: About 1.5 hours’ drive time

Highlights: Quabbin Reservoir; Gilberstville Village (Hardwick); Hamilton Orchards; New Salem 

Best season: Year-round 

8 – Old King’s Highway, Route 6A

Old King’s Highway, Route 6A

Old King’s Highway is perfect if you’re looking to be transported into pre-colonial times. Evidenced by four centuries of architecture along this route, the drive boasts American buildings that date back to the 17th, 18th, 19th, and 20th centuries. 

The little towns, shops, and cafes maintain the character of its historical significance. With many accolades received from National Geographic, this hits the nail on the hammer of scenic places in Massachusetts to explore and worth one of the best road trips in Massachusetts to take! 

Duration: About 1 hour 45 minutes’ drive time

Highlights: Pairpoint Glass; The Sandwich Boardwalk; Barnstable Centre; Coast Guard Heritage Museum; Brewster

Best Season: Year-round

Final Thoughts…

What did you think of our list of the eight best road trips in Massachusetts? Clearly, no number words in this post could fully describe the wonder of possibilities that lie in The Bay State. Ultimately, the best Massachusetts road trips are the ones that are waiting to be explored. Grab that pen and start charting your plans!

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Spare the trouble of planning and buckle up, because we’ve compiled the eight best road trips in Massachusetts for you to choose from! 

Spare the trouble of planning and buckle up, because we’ve compiled the eight best road trips in Massachusetts for you to choose from! 

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