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The rocky coasts and dense forests have been the backdrop for many stories and Hollywood productions. The tumultuous and ever-important history of the city of Boston played a major role in both the early and modern US.

Take a trip through this beautiful landscape, be it during the clear warmth of the summer, or perhaps the ever-changing colors of Massachusett’s crisp Fall. The Bay State is a beautiful destination for a road trip.

Day 1: Boston, MA

Boston is a city full of both historical and modern significance. It has been a city that is constantly transforming from its colonial routes to its present-day diversity, colleges, and incredible sports teams. There is 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 great little restaurant that is 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 started out 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

Related: 10 Road Trip Destinations In The South Perfect For BFFs

Day 2: Newburyport and the North Shore

Drive up the Massachusetts coast into the scenic beauty of the North Shore. Rocky forest-lined coast gives way to salt marshes and the aesthetic old towns such as Newburyport. Newburyport is home to a charming local culture, shopping centers in old mills, and beautiful beach-side attractions. Plum Island is a long narrow stretch of land with sand beaches easily accessible from Newbury or Newburyport. After the beach, take a trip back into the city and explore shopping centers like the Tannery Market Place and perhaps 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

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RiverWalk Brewing Co

Opening up 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 destination for spending an evening.

  • Address - 40 Parker Street Newburyport, MA 01950
  • Contact - (978) 499-2337, info@riverwalkbrewing.com
  • Beers
  • Menu

Newburyport Brewing Company

Offering a fantastic collection of beers, and being at the forefront of the movement to cans, Chris and Bill’s Newburyport Brewing Company is a great destination to visit. They are also both passionate about music and provide a relaxing atmosphere at their brewery.

  • Address - 4 New Pasture Rd, Newburyport, MA 01950, United States
  • Contact - (978)463-8700, info@nbptbrewing.com
  • Beers

Day 3: Western Mass, Deerfield to Northampton

Taking a trip west along route 2 will take you through Massachusetts’ thick forests until you reach Deerfield. Deerfield is the home of historical sites as well as great outdoor experiences. You can visit Historic Deerfield or hike up Sugarloaf for that iconic view of Western Massachusetts and the Connecticut River. Eventually, you will want to travel down I-91 a little to reach Northampton where you can enjoy its amazing variety of restaurants.

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

Travel Distance - 130 miles, 2 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 the location at the center of Northampton’s downtown along Main St. make it a local favorite.

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

The Brewery

Offering more than fine ales and lagers, The Brewery in Northampton offers a delicious variety of food and great service. Located just off Main Street, and conveniently next to 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

Related: Nova Scotia To Ontario: Guide To This Three-Day Road Trip

Day 4: Falmouth on the Cape

Now it's time to head back out east to one of the more renowned destinations in Massachusetts, and more specifically, Falmouth Massachusetts. This lovely town sits on the southern end of the cape and looks out at the stretch of water between it and Martha’s Vineyard. This town is home to a slower pace and seaside attractions. Take some time to enjoy this stunning seaside location.

Maison Villatte

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

  • Address - 267 Main St, Falmouth, MA 02540-2750
  • Contact - (774)255-1855, pain@maisonvillatte.com
  • Cost - $$-$$$
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Glass Onion

This is the essential coastal fine dining experience of Cape Cod. Enjoy the local flavors prepared in high-class mouthwatering dishes. Their local fish and shellfish are delicious and so 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 the time to check a few more items off of your must-do list while in the city again, now is the time to take advantage of it before the official end of your road trip.

  • Travel Distance - 72.2 miles, 1 hour 15 minutes
  • Google Maps
  • Total Distance Traveled - 402 miles
  • Total Time Traveled - 7 hr 20 min
  • Route Map