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Road Trips & Tours in Massachusetts

With windy back roads, tree-lined highways, and rustic natural beauty, New England was made for scenic drives. From incredible natural wonders in the Berkshires, to spooky sites over in Salem, fill up your tank and embark on a road trip through Massachusetts’ most scenic drives.

Coastal Lighthouses Road Trip in Massachusetts

The Massachusetts Atlantic coast is peppered with lighthouses from the tip on Cape Cod all the way to the tip of Cape Ann. Their towering stature which rises over rough waters have inspired everything from literature, to famous artwork, and even a few chilling ghost stories. Totaling just about a 9 hour drive along the coast with sparking blue waters as your backdrop, travel to some of the most awe-inspiring and charming lighthouses in Massachusetts on a seaside escape like no other.

Begin this road trip in Cape Cod, and head to Highland Light in Truro. As one of the oldest lighthouses in America, and Cape Cod’s first lighthouse, climb the 69-step hike to the top for panoramic views of the Atlantic Ocean. Take US-6 W to Nauset Lighthouse, made famous on every bag of Cape Cod Potato Chips. Get back on Main Street and follow to MA-28 N where you will find Chatham Lighthouse in Chatham, MA. Standing 48 feet tall, expect to always see this decorated for the holidays with a massive wreath. Get back on US-6 and drive to Nobska Light in Woods Hole, Martha’s Vineyard. Bring your camera along and snap a few pictures of the picturesque white picket fences, hydrangeas and sparkling water. Heading North up to Duxbury, follow the directions to MA-3 N to Glades Rd. There you will find Gurnett Light, first used in 1843 to guard the waters off of Gurnett Point. Still following the Atlantic coast north, arrive at Minot’s Ledge Light in Scituate. Built in 1860, this lighthouse still aids sailors in navigating the seas. Continue on MA-3 N to Boston Light on Little Brewster Island. As America’s oldest lighthouse, climb the 76 steps to the top of the lighthouse for unparalleled views.  Heading north all the way to Gloucester, visit Annisquam Light and hear the tale of the sighting of a massive sea serpent near the lighthouse about a decade after the beacon first shone. Finally, by way of MA-128, stop at Eastern Point Light located on Cape Ann. As one of the most iconic beacons in the state, it’s the perfect place to end your lighthouse road trip.

Fall Foliage Road Trips in Massachusetts

See the fall colors from the water as you take a ferry ride to Martha’s Vineyard, or head up to the Blue Hills Reservation in Milton – just south of Boston. Known for it’s incredible mountain summit, the Blue Hills Reservation is ideal for glimpses of the spectacular fall colors of nearby woodlands, not to mention incredible views of Beantown itself.

Western Mass is made for road trips, so take a drive through the Mohawk Trail, especially in autumn months to see some of the most beautiful fall foliage backdrops. Explore this historic scenic byway that winds and curves along northern Massachusetts via MA2 east to west.  The entire trail is 69 miles, but the most rewarding is the 37-mile long stretch between North Adam in the northern Berkshires, and Greenfield. Take the Mohawk Trail to the top of Mount Greylock for dramatic vistas. Drive through the rolling hills of the Berkshires and head west, making many stops along the way.

Day Trips From Boston, MA

With Boston as home base, hop in the car and drive to Concord, Lexington and Lincoln, MA for a quick and easy history lesson. Just about a 40-minute drive, follow the path of the American Revolution and head to famous battlegrounds at Minute Man National Historical Park. Stroll the Battle Green, known as Lexington Town Common, where the shots that began the Revolution were fired, and visit The Lexington Minuteman statue, The Old Burying Ground, the North Bridge, The Concord Museum (Paul Revere’s lantern), the 1747 Wright’s Tavern, and Sleepy Hollow Cemetery, where Thoreau, Emerson, Hawthorne, and the Alcotts (father and daughter) are buried on Authors Ridge.

Take a day trip to Boston’s South Shore and visit Nantasket Beach in Hull, about 1 hour south of Boston. With water bordering on three sides, this seaside town has a charm all of its own. Spanning five miles of sand nestled on the Atlantic, swim, frolic, rent a boat, and paddle the Weir River Sanctuary for glimpses of herons, egrets, and osprey.
The Hull Lifesaving Museum follows the history of Boston Harbor, from shipwrecks to dramatic rescues, with views of Boston Light lighthouse from the cupola. Enjoy the quaint shopping, art galleries, and the Paragon Carousel, one of the oldest in the country, all at Nantasket.