• Natalie Nicole Wilson

19 Day Trips From Boston


The day trips have to be one of my favorite things about living in Boston and New England in general. Growing up in Tennessee, there are few day trips under 4 hours away. I have taken full advantage of this luxury, and I'm stoked to share some of the greatest day trips from Boston with YOU.


A few things to note - I have arranged the day trips in order from closest to further away from Boston, I have ++ the destinations I feel need more than just a day, and italicized the destinations I have not gotten to just yet but will be making it to soon.


1. Salem, MA (34 minutes)

Nobody does Halloween like Salem! Best known for their 1692 witch trials, this New England coastal town attracts tourists from all around the world every fall to experience their haunted happenings. Driving around the city, you may see familiar scenes from the popular movie, Hocus Pocus, a Halloween classic, or people wearing fun costumes.


Although the fall festivities are fun, the historic town is filled with interesting stories of past witchcraft, executions, and real-life witches. And you thought it was just a bunch of Hocus Pocus ..


2. Plymouth, MA (41 minutes)


Plymouth, the first colonial settlement in New England, holds a ton of history for the history buffs out there. Founded in 1620, you can explore where the newcomers landed the Mayflower. The Mayflower II is a replica that allows visitors to climb onboard and further learn about their voyage to America. Pretty cool.


If you're not into American history, enjoy their beautiful beaches. We are excited for our visit


3. Newburyport, MA (43 minutes)


This small, seaport town just north of Boston, makes for a fun stop to stretch your legs. Whether heading further up into Maine or even New Hampshire, stop by Newburyport for a coffee, waterfront dining, and a little shopping.


4. Gloucester (43 minutes)


Known as "Americas Oldest Seaport" and, at one point, America's largest fishing port, Gloucester is most known for its fishing and whale watching.


You can also take a stroll down Gloucester's Main Street, where you will find local and well-known shops, fresh seafood, and coffee shops.


This cute little town is best paired with Rockport, MA. A little tip - take the scenic route to Rockport vs the interstate. It may add a couple of minutes, but it's totally worth it. The street you want to take is Thatcher Rd, I believe.


5. Rockport, MA (48 minutes)

Rockport is a must, must, must if you live or are traveling close to Boston. Rockport has so much character and is truly picture perfect. It's everything you think of when you think of New England.


The picturesque town hosts the Motif #1, the most often painted building in America. Believe it or not, in the 1840s the shack held fishing supplies and fishermen's daily catches. While you're visiting you may even catch an artist in mid-work painting. I did!


There are restaurants galore, ice creme parlors, and beautiful nearby neighborhoods to explore. You can also find fun gifts for friends and family in one of their many shops. As always, the beaches are a good option, too.


6. Portsmouth, NH (1 hr)


Right on the border of New Hampshire and Maine, you will find one of the most hoppin' towns in New Hampshire. Its charm is best enjoyed on a beautiful day, dining waterfront with a nice stroll down the main drag. Trust me when I say it will be hard to choose a dinner spot with the variety offered.


I love going on a nice hike further up into New Hampshire or to the beach in Maine and then stopping in Portsmouth on the way home for dinner at sunset.


6. Ogunquit, ME (1 hr 14 min)

Home to my personal favorite lobster roll, Ogunquit makes for a perfect day off spent relaxing.


First and foremost, you must go get a lobster roll from Foot Bridge Lobster in Perkins Cove. 10/10, I tell ya.


After your lobster drunk, go and enjoy the rest of the day at Ogunquit Beach. There are numerous walk-up windows to grab a drink nearby (just put it in a cup on the beach ;))


Truly my favorite spot for a lazy day in the sun.


7. Newport, RI (1 hr 14 min) ++

Newport can be done as a day trip if you are okay with not getting around to everything. This city is definitely better explored over a weekend. However, if you only have a day - make the most of it!


The Cliffwalk is a must. 3.5 miles long, I wouldn't recommend walking the entire thing with only a day to spare, but definitely check it out for at least a half-hour. The views are incredible and you may even get to watch the surfers rip some waves.


The mansions are also a gotta see. If you are limited to just a day, enjoy the walkthrough audio tour of The Breakers and The Elms, the most popular mansions.


The main street in Newport is the place to be on the weekends. There are plenty of dining options and an outside bar to grab a drink and sit by the water. If you prefer a coffee or some delicious baked goods, try out Coffee Grinders. During the summer, the restaurants will have a wait anywhere you go, but don't worry! They have some pretty good retail shops to browse through while you're waiting.


The sunset champagne cruise is a fabulous way to end your day trip. Watching the sunset with a glass of champagne - nothing beats it. Just make sure to bring a light jacket.


8. Falmouth, MA (1hr 15 min)


Cape Cod has some of the most beautiful beaches in New England.


Whether basking in the sun, enjoying a glass of wine at Cape Cod Winery, or catching the ferry over to Martha's Vineyard - check this place out! We can't wait.


9. Jamestown, RI (1hr 21 min)


Although Newport needs a day of its own, Jamestown is a nice town to see along with Newport as it is just over the Newport Bridge.


Visit the Beavertail Lighthouse and Ford Wetherill State Park for some Rhode Island beauty.


10. Kennebunkport, ME (1 hr 31 min)

Summer home to the former president, George W. Bush, this coastal Maine town is stunning.


Besides shopping, eating, and beaching, you could easily get lost looking at the beautiful shoreline homes.


Kennebunkport is best paired with the larger city, Portland, ME.


11. Matunuck, RI (1 hr 32 min)

Matunuck is such an underrated RI town. Home to one of the best oyster bars in the US, Matunuck Oyster Bar, if you only drive up for this meal - you've had a day trip well spent.


Matunuck Beach is one of my personal favorites beaches in New England and a very popular summer destination for local New Englanders.


Point Judith, close by, is where you can catch the ferry to Block Island, another fun day trip option.


12. Westerly, RI (1 hr 33 min)


Summer home to pop legend, Taylor Swift, Westerly is a beautiful town to enjoy while passing through to other destinations.


A very ritzy town, the best thing to do is enjoy the pretty beaches and admire the seaside mansions.


13. Mystic, CT (1 hr 37 min)

There is so much to admire in Mystic. One of my favorite spots in Connecticut, Mystic offers a variety of fun.


Walk across one of the oldest draw bridges in the US, the Mystic River Bascule Bridge, that is still utilized to this day.


Historic downtown mystic is a place to enjoy waterfront dining and shopping. After lunch, walk over to their very popular Mystic Aquarium, one of their museums, or enjoy a nice boat tour.


14. Portland, ME (1 hr 42 min) ++

This is another city that you could enjoy over a weekend. There is so much to see and do.


Old Port, the beating heart of this city, is a nice place to start. There are several streets of unique shops, fresh lobster rolls and other delicious cuisines, bars and taverns, coffee shops, and anything else you may be searching for. It's a very walkable city, so get out there.


Hard to do with just a day but definitely worth looking into for longer stayers, Casco Bay Islands. These are a group of islands right outside of Portland, most of them accessible by ferry year-round. You can get on and off at the different islands, but I enjoyed staying on and watching them load and unload cargo at the different stops. Mail looks a little different over here.


Cape Elizabeth, just 9 or so miles out of Portland, is home to the most photographed lighthouse in the US and some say the entire world. It's a sight to see and worth venturing out to.


15. Wolfboro, NH (1 hr 47 min)

Every time I go to New Hampshire I'm constantly stunned by its beauty and hidden treasures. Located right on Lake Winnipesaukee, you will be blown away, too.


Mount Major, a moderate hike right outside the town, offers beautiful views of the lake. Pups are allowed, too.


If hiking is not your thing, boat rentals, kayaking, and paddleboarding are awesome options as well.


16. Provincetown, MA (2hr 5 min)

The famous Commercial Street is an obvious must. From here, Racepoint Beach is relaxing and perfect for catching rays.


Feeling more adventurous? Take a dune tour or enjoy their plentiful bike trails.


17. Martha's Vineyard, MA (2 hr 35 min)


An island south of Cape Cod, this is a must-visit. I can't wait to update you on the must-dos in a short week!


18. Block Island, RI (2 hr 45 min)

Still able to fit this in during a day trip, this would be a fun overnight stay. You can take the 55 minute or 30-minute ferry from Narragansett, RI to the island. The ferry has snacks and drinks, non-alcoholic and alcoholic, for sale during cruise time.


Once on the island, enjoy the sunshine on the beach or lunch at one of the many Inns with panoramic views.


Spend a couple of hours taking in the spectacular views at Mohegan Bluffs - my favorite spot.


19, Nantucket, MA (2 hr 50 min)


Nantucket is another island that I will be visiting in the next couple of weeks. You can catch an hour ferry from Hyannis, MA. More to come on this adventure.


Miss a good day-trip destination? Drop it in the comments. I will be updating this post on the places I have not made it to just yet.


Nat

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