Top 10 Scenic Drives in Massachusetts

Massachusetts may be one of the smaller states in the country by land mass, but it is huge on preserved history and natural beauty. The area played a pivotal part in American history from the Pilgrims landing at Plymouth Rock to the Salem Witch Trials to the start of the Revolutionary War, and various historical markers and even living museums can be found throughout the state. There are also several types of landscapes present in the area despite its small size, including coastal plains, rural hills, and the Berkshire Mountain Range. With all that Massachusetts has to offer, it can be difficult to decide where to begin an exploration of this state. That’s why we’ve compiled a list of our favorite Massachusetts scenic drives to provide a starting point for your adventure:

No. 10 – Chickatawbut Road

Chickatawbut Road Massachusetts
Flickr user: Geoffrey Coelho

Starting Location: Braintree, MA
Ending Location: Milton, MA
Length: 6 miles
Best Season to Drive: All
See this drive on Google Maps

This easy drive on the Chickatawbut Road just outside of Boston is a great reminder of the natural wonders that often lie just out of view in urban settings. Passing through verdant woods and craggy summits with views of the city, it’s hard not to notice the blue-ish tinge to the vegetation, earning the region the name of the Blue Hills. Kids may enjoy the educational Blue Hills Trailside Museum, which also has live animals, while all ages can appreciate the recreational opportunities at The Blue Hills Reservation.

No. 9 – Central Hills Loop

Central Hills Loop Massachusetts
Flickr user: D.R.Davis

Starting Location: New Salem, MA
Ending Location: New Salem, MA
Length: 57 miles
Best Season to Drive: Fall
See this drive on Google Maps

Enjoy the back roads in the Central Hills region of the state and views of the Quabbin Reservoir on this charming loop through New Salem. The largely pristine landscape is full of dense forests, rolling hills, and unusual rock formations to dazzle the eye. In the village of Gilbertville in Hardwick, check out its historic covered bridge, then head off to Hamilton Orchards, where you can pick your own seasonal fruits.

No. 8 – Mount Greylock

Mount Greylock Massachusetts
Flickr user: Massachusetts Office of Travel & Tourism

Starting Location: Pittsfield, MA
Ending Location: Adams, MA
Length: 17 miles
Best Season to Drive: All
See this drive on Google Maps

Culminating at Massachusetts’ highest point of Mount Greylock, expect panoramic views to unleash your inner photographer or inspire athletic types to take a nearby hike. Before reaching the summit, however, there are other places of note to explore. The War Memorial Tower pays homage to the fallen soldiers throughout the area’s history, and the 1930s Bascam Lodge overlooks the same views that inspired Thoreau to write, “It was such a country as we might see in dreams, with all the delights of paradise.”

No. 7 – Northern Berkshires

Northern Berkshires Massachusetts
Flickr user: anslatadams

Starting Location: Sunderland, MA
Ending Location: Williamstown, MA
Length: 53 miles
Best Season to Drive: All
See this drive on Google Maps

This route through rural Massachusetts and Savoy Mountain State Forest not only delights the eye but soothes a harried mind with its tranquil scenes. Get a taste of what life was like in Colonial New England with a stop at Historic Deerfield, where its residents strive to preserve that culture with its traditions. Art enthusiasts will want to investigate North Adams with its varied mix of galleries and art studios, including River Hill Pottery and  MASS MoCA, a performing arts center inside a 19th century factory that has been restored.

No. 6 – Plymouth County

Plymouth County Massachusetts
Flickr user: Massachusetts Office of Travel & Tourism

Starting Location: New Bedford, MA
Ending Location: Plymouth, MA
Length: 50 miles
Best Season to Drive: Fall
See this drive on Google Maps

Allow ample time to investigate the sites off-road – as much as an entire weekend – because many of the available experiences are of once-in-a-lifetime status. Start at the New Bedford Whaling National Historic Park, which educates visitors about the area’s whaling history and maintains several historic buildings on its grounds. Stop in Wareham in the fall for a cranberry bog tour at the A.D. Makepeace Company, then take a whale-watching excursion or visit Pilgrim Memorial State Park and Plymouth Rock near the end of the trip.

No. 5 – Revolutionary War Tour

Revolutionary War Tour Massachusetts
Flickr user: Peter Lee

Starting Location: Lexington, MA
Ending Location: Concord, MA
Length: 7 miles
Best Season to Drive: All
See this drive on Google Maps

Although the drive is quite short, the historical landmarks relating to the Revolutionary War make this trip worth noting, and – with stops – it could easily pass a morning or afternoon. Visit the Minute Man National Historic Park to learn more about the skirmishes in the area that sparked the war. Don’t miss the opportunity to photograph Concord ‘s Colonial Inn, built in 1716 and operating to this day as a hotel.

No. 4 – Southwest Berkshires

Southwest Berkshires Massachusetts
Flickr user: Massachusetts Office of Travel & Tourism

Starting Location: Sheffield, MA
Ending Location: Pittsfield, MA
Length: 27 miles
Best Season to Drive: Spring, Summer, Fall
See this drive on Google Maps

This route at times skirts the October Mountain State Forest and, at others, runs the edge of Pittsfield State Forest with plenty of opportunities to get outside and forge an intimate bond with nature. In Lenox, art lovers may enjoy a tour of the the Frelinghuysen Morris House & Studio, a 46-acre estate with an outstanding Cubist art collection. In Pittsfield, don’t miss the living history attraction Hancock Shaker Village that transports visitors back in time from April to October.

No. 3 – Cape Ann

Cape Ann, Massachusetts
Flickr user: Ollie Jones

Starting Location: Salem, MA
Ending Location: Rockport, MA
Length: 21 miles
Best Season to Drive: All
See this drive on Google Maps

Following the rocky cape on the Atlantic Ocean, this drive has no shortage of seaside views of fishing boats, New England architecture, and lighthouses. Stop in Gloucester for a whale-watching tour, where humpback, blue, and the endangered North Atlantic right whales are commonly spotted. In Halibut Point State Park, unleash your inner photographer on the 440-million-year-old rocky ledges which provide fantastic views of the area.

No. 2 – Mohawk Trail

Mohawk Trail, Massachusetts
Flickr user: Maia C

Starting Location: Greenfield, MA
Ending Location: Williamstown, MA
Length: 42 miles
Best Season to Drive: All
See this drive on Google Maps

On this route that was once a Mohawk Native American footpath, there are countless scenic areas that afford the opportunity to hike, ski, kayak, or canoe to see the area in an up-close-and-personal manner. See what life was like for early residents in 1895 at Old Greenfield Village, which strives to be as historically accurate in its buildings as possible. The Barton Cove Recreation Area in Gill has a one-mile nature trail down the river that leads to a dinosaur footprint quarry to go even further back in time.

No. 1 – Old King’s Highway

Old King’s Highway Massachusetts
Flickr user: Rick Harris

Starting Location: Sandwich, MA
Ending Location: Provincetown, MA
Length: 59 miles
Best Season to Drive: Summer, Spring, Fall
See this drive on Google Maps

Cape Cod is known for its unspoiled beaches and sleepy historic towns, and this scenic drive takes travelers right through the heart of it. Although there are numerous spots to stop and enjoy the ocean, Town Neck Beach and Sandy Neck Beach are local favorites. Nickerson State Park has some freshwater ponds good for fishing, and the Wellfleet Bay Wildlife Sanctuary is a birdwatcher’s paradise and is home to many rare plants.


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