5-Day Bucket-List Road Trip Circuit: Explore Massachusetts

Shutterstock

Quick Links

  • Day 1: Boston, MA
  • Day 2: Newburyport and the North Shore
  • Day 3: Western Mass, Deerfield to Northampton
  • Day 4: Falmouth on the Cape
  • Day 5: Back to Boston

The rocky coasts and dense forests happen to be the backdrop for a lot of stories and Hollywood productions. The tumultuous and ever-important history of the town of Boston played a major role both in the early and modern US.Take a trip through this beautiful landscape, be it during the clear warmth of the summer, or maybe the ever-changing colors of Massachusett’s crisp Fall. The Bay State is really a beautiful destination for a road trip.

First day: Boston, MA

Boston is a city full of both historical and modern significance. It's been a town that is constantly transforming from its colonial routes to the present-day diversity, colleges, and incredible sports teams. There's much to explore in this city from its more tourist-centric Quincy Market to its museums and Aquariums.

Must-Visit – Quincy Market, Freedom Trail, John F. Kennedy Presidential Museum & Library, Sam Adams brewery

Mario's Restaurant

Mario’s is a superb little restaurant that's positively reviewed by the surrounding community. It has been running for 38 years providing excellent service and delicious food to its community.

  • Address – 347 Chelsea St, Boston, MA 02128-1480
  • Contact – (617)567-8608
  • Cost – $$-$$$
  • Must-Try – Prawn linguine
  • Menu

North Street Grille

Making use of heirloom recipes, North Street Grille began with the dream of creating a friendly and delicious dining experience. Owner Robin Sidell opened North Street Grille in 2004 and since then it has become a go-to neighborhood destination.

  • Address – 229 North St, Boston, MA 02113-2105
  • Contact – (617)720-2010
  • Cost – $$-$$$
  • Must-Try – Eggs benedict
  • Menu

Day 2: Newburyport and the North Shore

Drive up the Massachusetts coast into the scenic great thing about the North Shore. Rocky forest-lined coast gives method to salt marshes and the aesthetic old towns such as Newburyport. Newburyport is home to a captivating local culture, shopping malls in old mills, and beautiful beach-side attractions. Plum Island is really a long narrow stretch of land with sand beaches easily accessible from Newbury or Newburyport. Following the beach, vacation into the city and explore shopping centers such as the Tannery Marketplace and maybe enjoy a show at the Actors Studio of Newburyport.

Must-Visit – Plum Island, The Actors Studio of Newburyport, Custom House Maritime Museum

Travel Distance – 37.7 miles, 45 minutes

Google Maps

RiverWalk Brewing Co

Opening in 2012, RiverWalk Brewing Co has provided balanced yet complex craft beer to its community in Newburyport. Offering both outstanding beers and dining, RiverWalk Brewing Co is a great place to go for spending a night time.

  • Address – 40 Parker Street Newburyport, MA 01950
  • Contact – (978) 499-2337, [email protected]
  • Beers
  • Menu

Newburyport Brewing Company

Offering a fantastic assortment of beers, and being at the forefront from the movement to cans, Chris and Bill’s Newburyport Brewing Company is an excellent location to visit. They are also both passionate about music and supply a calming atmosphere in their brewery.

  • Address – 4 New Pasture Rd, Newburyport, MA 01950, Usa
  • Contact – (978)463-8700, [email protected]
  • Beers

Day 3: Western Mass, Deerfield to Northampton

Taking a visit west along route 2 will take you through Massachusetts’ thick forests before you reach Deerfield. Deerfield is the home of historical sites in addition to great outdoor experiences. You can go to Historic Deerfield or hike up Sugarloaf for your iconic look at Western Massachusetts and the Connecticut River. Eventually, you will want to travel down I-91 just a little to achieve Northampton where you can enjoy its amazing number of restaurants.

Must-Vist – Historic Deerfield, South Sugarloaf Trail, Thornes Marketplace

Travel Distance – 130 miles, A couple of hours 36 minutes

Google Maps

Fitzwilly’s

For 40 years Fitzwilly’s has been a staple of Northampton’s dining experience. Their quality food, excellent selections, chill atmosphere, and also the location at the center of Northampton’s downtown along Main St. turn it into a local favorite.

  • Address – 23 Main St, Northampton, MA 01060
  • Contact – (413)584-8666
  • Cost – $$-$$$
  • Must-Try – Wicked Alfredo
  • Menu

The Brewery

Offering a lot more than fine ales and lagers, The Brewery in Northampton offers a delicious number of food and great service. Located near Main Street, and conveniently alongside a public parking lot, The Brewery has been a go-to spot in Northampton's downtown for 34 years.

  • Address – 11 Brewster Ct, Northampton, MA 01060-3801
  • Contact – (413)584-9903
  • Cost – $$-$$$
  • Must-Try – Catfish Bites
  • Beers
  • Menu

Day 4: Falmouth around the Cape

Now it's time to return out east to one from the more renowned destinations in Massachusetts, and much more specifically, Falmouth Massachusetts. This lovely town sits around the southern end from the cape and appears out at the stretch of water between it and Martha’s Vineyard. The town is home to a slower pace and seaside attractions. Take some time to savor this stunning seaside location.

  • Must-Vist – Shining Sea Bikeway, Nobska Point Lighthouse, Old Silver Beach
  • Travel Distance – 158 miles, A couple of hours 37 minutes
  • Google Maps

Maison Villatte

This French-style bakery and café offers many wonderful and delicious treats to select from. Take your time and spoil yourself as you pick from their number of delicious treats.

  • Address – 267 Main St, Falmouth, MA 02540-2750
  • Contact – (774)255-1855, [email protected]
  • Cost – $$-$$$
  • Social Media

Glass Onion

This may be the essential coastal fine dining experience with Cape Cod. Enjoy the local flavors prepared in high-class mouthwatering dishes. Their local seafood are delicious and they are their desserts and beverages.

  • Address – 37 N Main St, Falmouth, MA 02540-2843
  • Contact – (508)540-3730
  • Cost – $$$$
  • Must-Try – Lobster strudel
  • Menu

Day 5: Back to Boston

The drive up along the South Shore to Boston is itself an experience. If you still have time to check a few more items off of your must-do list whilst in the city again, this is the time to consider benefit of it before the official end of your road trip.

  • Travel Distance – 72.2 miles, 1 hour Fifteen minutes
  • Google Maps
  • Total Distance Traveled – 402 miles
  • Total Time Traveled – 7 hr 20 min
  • Route Map