Growing up just outside of the city,  I like to think I have perfected the art of day trips from Boston, MA. While the city itself is wonderful, it can be nice to hop in the car and explore a bit further out. Particularly in nicer weather, a day trip is just what the doctor ordered! 

From the North Shore to the South Shore and a bit further out, here are some of the best day trips from Boston, MA:

North Shore

Looking to go for a gorgeous drive with a pit stop or two along the way? The Essex Coastal Scenic Byway is a 90-mile-long roadway connecting Massachusetts communities like Rockport, Gloucester, Manchester-by-the-Sea and Salem. 

Each town has its own unique history and selling points, but Rockport is one you certainly won’t want to skip. Take some time on your day trip to explore the quintessential summer destination.

rockport MARockport 

One of the first sights you’ll see when roaming the town is Motif No. 1. The red fishing pier is a Rockport staple, sitting right on the waterfront and giving off charming New England vibes. Fun fact: it is the most painted building in the world. You’ll definitely want to snap a few photos here!

Sandy Bay’s Front Beach is open to visitors and locals year round, and is certainly worth a visit. A quick walk from downtown Rockport, you can easily bounce back and forth from the water to the village.

Rockport downtown village is known for its many wonderful eateries, like Roy Moore Lobster Company for quality seafood and fresh cooked lobster. After you’ve finished your meal, head to the Rockport Brewing Company to finish off your delicious meal with a pint (or two)!

ice cream store in rockport MA

When looking for a sweet treat, I love to stop by The Ice Cream Store. This aptly named little creamery on the water is super popular, and for good reason! Not only is it quaint, but the many ice cream flavor offerings will hit the spot.

Newburyport

Newburyport is also within the Essex Coastal Scenic Byway, but it deserves to be one of its own day trips from Boston, MA! It is home to Plum Island, an adorable area off the coast of Cape Ann. Take Instagram-worthy pictures of the lighthouse, then make your way to one of the stunning state parks or trails.

newburyport MA

The Parker River National Wildlife Refuge is a refreshing gem in Newburyport. Established in 1941 to provide a nesting habitat for migratory birds, you’ll find a diverse landscape of sandy dunes, cranberry bog, and freshwater marsh. It’s probably the best spot for photography in the area!

Maudslay State Park is also a breathtaking natural landscape with 19th century gardens and plantings. Take a leisurely walk or rent a bike to really take in the sights. Better yet, if you have time, plan a picnic. If you’re a MA resident, the parking fee is only $5, so best to make a day of it!

Once walking has you worn out, grab a pint from Newburyport Brewing Co. After all, the best day trips end up at a local brewery.

South Shore 

As a South Shore native myself, I am quite passionate about including the area when discussing the best day trips in Boston. MA is full of beautiful spots, and the South Shore has many quaint towns right on the water to explore!

Hingham

Hingham is a cute little town with a colonial feel, settled on the waterfront of Boston Harbor. There are lots of things to do, and one of the most popular is to visit the Derby Street Shops. The upscale outdoor outlets include stores like Anthropologie, J Crew and Lululemon.

World’s End park is also a tourist favorite. Offering up sweeping views of the Boston skyline, it’s no wonder there’s so much buzz around this park. Plus, the landscape was designed by the famous Frederick Law Olmsted, so you know the trails are top-notch!

Main Street is a fun stretch of cafes, restaurants, boutiques and even an old-timey movie theatre. Brewed Awakenings is one of my all-time favorite coffee spots, with an extensive menu and mouth watering selection of pastries. And who doesn’t love a good coffee pun?

coffee shop hingham

If you end up in Hingham around dinner time, check out Alma Nove. This waterfront restaurant is inspired by flavors from Italy and the Mediterranean. It also happens to be named after the Wahlberg family matriarch, which is how you know you’re not too far from Boston! 

Plymouth

Many tourists travel to Plymouth with eager anticipation to see the Plymouth Rock. And while most times, this experience is a bit underwhelming, the town still has a lot to offer when it comes to day trips from Boston, MA!

This coastal town is acclaimed for its popular seafood restaurants, like Cabby Shack right by the entrance to the harbor. However, there are other excellent eateries, like KKatie’s Burger Bar for a casual (but life changing!) burger, or East Bay Grille for an upscale, classic New England dining experience.

There is a jetty right on the Plymouth Harbor, allowing you to go for a nice stroll while taking in the gorgeous views.

plymouth harbor MA

Of course, if you’re looking to immerse yourself in history on your day trip, you’ll want to visit Plimoth Plantation. The recreation of the pilgrim’s original settlement is a fun and interactive way to learn more about the rich history of the town.

And Beyond:

Cape Cod

One of the most beloved day trips from Boston, MA is a day spent on the Cape! There are multiple towns worth checking out. Here’s the general breakdown according to their official website:

  • Upper-Cape: Falmouth, Mashpee, Sandwich, Bourne
  • Mid-Cape: Dennis, Yarmouth, Barnstable
  • Lower-Cape: Brewster, Chatham, Harwich, Orleans
  • Outer-Cape: Eastham, Wellfleet, Truro, Provincetown

I personally recommend the Outer-Cape for a day trip, as it feels a bit more separated from the busier towns. 

Provincetown, or P-town, is a trendy and popular summer destination. The vibrant town is less than a 3 hour drive from Boston, but you can also opt to take a ferry ride over instead. That option is a bit pricier, but of course offers more time on the water with pretty views. Plus, you can skip out on that Massachusetts traffic!

Commercial Street is where all the action is. Its East End is home to a number of art galleries, as well as the Provincetown Art Association & Museum. When you need a caffeinated pick-me-up after walking around all afternoon, the Wired Puppy won’t disappoint.

The West End of Commercial Street feels a bit more abuzz with restaurants and shops. It’s a colorful and lively area with no shortage of people-watching opportunities.

Ogunquit, ME

About a two hour drive from the city, high on my list of day trips from Boston, MA is Ogunquit, Maine. On the southern coast of Maine, Ogunquit’s motto is “beautiful place by the sea.” If that hasn’t convinced you to visit yet, here are some specific recommendations:

cliff house hotel maine

The Cliff House Resort and Spa is one of the most gorgeous hotels I’ve ever stayed at. Nautical decor adorns the lobby and rooms, reminding you that you are never far from the water. The amenities aren’t too shabby either, with an indoor pool and two outdoors. There is also a luxury spa and access to a course at the Cape Neddick Golf Club.

Be sure you include a walk along Marginal Way on your day trip itinerary. This coastal path keeps you right near the water, and will land you in the adorable Perkins Cove area.

Perkins Cove

Away from the busy beach, you’ll never want to leave this little fishing cove. There are many eateries overlooking the ocean, but my dinner at Jackie’s Too was one of those experiences you never forget. The food and service was impeccable, and I’ve been dying to go back ever since! 

Luckily, all of these locations are under a 3 hour drive from Boston, making it easy enough to hop in the car and spend a day touring these new destinations.

Do you prefer the North Shore or South Shore? What’s your favorite town on Cape Cod? What is your ideal day trip in Massachusetts?

Sara Frazier

Author Sara Frazier

More posts by Sara Frazier

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