13 Awesome Family Day Trips in Massachusetts By Season

Looking for the best family day trips in Massachusetts?

I often get stir-crazy with my daughter on the weekend and find that the best solution is to get out and explore somewhere new!

Taking day trips in Massachusetts as a family always feels like a win-win: my husband and I get to satisfy our wanderlust, even if just for a short period of time, and our daughter gets the benefit of experiencing new places and activities, too.

So without further ado, here are 13 of the best family day trips in Massachusetts.

Family Day Trips in Massachusetts: Summer & Fall

I’ve grouped these family day trips in Massachusetts into sections by seasons: summer/fall and winter/spring. While a lot of these places are nice to visit any time of year, there are seasonal activities and events that make them especially fun at a certain time.

Here are some great family day trips for the summer and fall:

1. Nantucket

My parents took me and my brother to Nantucket when we were teenagers and it was unforgettable. We rented a small cottage for a week and rode bikes all over the island and took “The Wave” shuttle bus to the best beaches.

Even though you could spend a few days or longer on Nantucket, you could easily make a day trip out of it as well. There is a high-speed ferry from Hyannis that will get you there in just one hour.

Your kids are sure to see it as an adventure to escape to an island for a day. You get the sense that you’re in another world for a little while!

Family Fun Things To Do

⭐️ Play on the beach: There are several great beaches on Nantucket, including Surfside Beach, Madaket Beach, and Siasconset Beach. If you have young children, Children’s Beach is on the harbor side of Nantucket and has much calmer water and a nice playground.

⭐️ Learn about life as a whaler: Older kids might appreciate touring the Whaling Museum and learning what life was like for whalers living on Nantucket over the centuries.

⭐️ Go lighthouse hopping: Hunt for Nantucket’s three different lighthouses on different parts of the island — Brant Point Lighthouse, Sankaty Point Lighthouse, and Great Point Lighthouse.

⭐️ Search for sea life: Explore more than 16 miles of sandy trails at Coskata-Coatue Wildlife Refuge. Along the beachfront, you’re likely to spot horseshoe crabs, seals, a variety of birds, and other marine life!

⭐️ Hike the Sconset Bluff Walk: This unique, public trail winds through the backyards of private homes, with impressive ocean views scattered along the way.

For a list of other family-friendly beaches in Massachusetts, check out 13 Best Beaches in Massachusetts for Families.

2. Gloucester

Gloucester is a beautiful coastal town about 32 miles northeast of Boston. It’s located on Cape Ann and isn’t far from another great family destination: Rockport (recommended in #3!).

We went to Gloucester for a summer beach day and had an amazing time. If you and your family are interested in spending a day by the ocean, Gloucester makes for the perfect getaway.

Family Fun Things To Do

⭐️ Have fun in the sun at Good Harbor Beach: This is the most popular beach in Gloucester and it’s very family-friendly. It gets crowded in the summer but there are still plenty of parking spaces in the nearby lot.

🚗 You’ll need to reserve a parking spot ahead of time for about $35 a day.

⭐️ Indulge yourselves at Holy Cow Ice Cream Cafe: I once saw an Instagram post asking for the best ice cream places in Massachusetts, and Holy Cow came up numerous times in the comments. We tested it for ourselves and can confirm: it’s DELICIOUS.

⭐️ Grab fish and chips from Turner’s Seafood: We stumbled across this place while driving through town, and it turns out they have the most delicious fish and chips. You can tell it’s where the locals go for their seafood — definitely a must-try!

⭐️ Tour a medieval castle: Did you know Massachusetts has its own castle? Hammond Castle, located right on the coast, is the former residence of scientist and inventor John Hays Hammond and is open for public tours.

🎟 Castle tickets cost $20 for adults and $10 for kids ages 5-12 (free for kids 4 and under).

⭐️ Go on a whale watching tour: Gloucester is one of the best places in Massachusetts to spot whales. Book a tour with 7 Seas Whale Watch, a family-run business that has been around for more than 70 years.

Check out my full post, 13 Fun Things to Do with Kids in Gloucester, MA, for more ideas!

3. Rockport

Just four miles north of Gloucester is another popular North Shore beach town: Rockport. If you have a hard time deciding between Gloucester or Rockport as a day trip, you could easily visit both!

There’s no shortage of outdoor fun to be had in Rockport. From sandy beaches and scenic trails to fresh lobster rolls and ice cream, you’re sure to make long-lasting memories in this New England hot spot.

Family Fun Things To Do

⭐️ Chow down on fresh seafood: You can’t be this close to the ocean and not enjoy a local catch! Both Roy Moore’s and The Lobster Pool have rave reviews for their seafood.

⭐️ Bike or kayak around Cape Ann: If you want to keep things active, rent bikes or kayaks from North Shore Kayak & Bike Adventures to explore Cape Ann on land or sea.

⭐️ Enjoy the sand and surf: Long Beach and Front Beach are two of the most popular beaches in Rockport and are great places to spend a few hours soaking up the sun with the family.

⭐️ Grab some ice cream at Bearskin Neck: The Ice Cream Store, Gifford’s and Sundays are all great ice cream options in this cute little part of Rockport. Be sure to also catch a view of the iconic red fishing house nearby, Motif #1.

⭐️ Go bird watching at Halibut Point: Hike the granite ledges of this beautiful state park near the ocean and keep your eyes open for a variety of birds and other wildlife.

4. Plymouth

Plymouth is a great day trip choice if you want a more historic and educational experience for your family. This coastal town is known for being the site of the first Pilgrim settlement and has several family-friendly places to check out.

Family Fun Things To Do

⭐️ See Plymouth Rock: Check out the site that is said to be where the Pilgrims first landed in 1620 (after a brief stop on Cape Cod).

⭐️ Visit Plimoth Patuxet Museums: This living history museum is made up of two main exhibits, the Plimoth Plantation and the Wampanoag Homesite. Plimoth Plantation recreates a Pilgrim village with costumed interpreters who portray what daily life looked like in the 1600s.

Similarly, the Wampanoag Homesite recreates a traditional Wampanoag village, where you can learn about the language, food, and clothing of Plymouth’s native inhabitants.

⭐️ Take a cranberry farm tour: Learn how Massachusetts’ number one food crop is cultivated by visiting a working cranberry bog. Massachusetts Cranberries hosts bus tours April-November and public harvest tours during weekends in October.

⭐️ Go kayaking: Billington Sea Kayak is on the shores of Billington Sea, a large inland lake in Plymouth. You can choose from kayak, canoe, or paddleboard rentals for some water fun.

⭐️ Play at Nelson Memorial Park: Enjoy this waterfront green space with a large playground and splash pad for kids to enjoy.

5. Cape Cod

Cape Cod is one of the most popular summer destinations in Massachusetts, and it’s easy to understand why with its many beaches and outdoor attractions. It’s only about 70 miles from Boston and easily accessible from other parts of the state as well.

If you go to Cape Cod during the busy summer months, be prepared for heavy traffic along the way, but once you arrive, it’s worth it!

Family Fun Things To Do

⭐️ Enjoy a beach day: There are lots of awesome beaches on Cape Cod. Coast Guard Beach is one of my favorites, with great waves and soft sand.

⭐️ Picnic at Keyes Memorial Beach: Located on the Nantucket Sound side of Cape Cod, this beach has a grassy hill nearby that makes for a nice family picnic location.

⭐️ Go whale watching: Hyannis Whale Watcher Cruises is one of the best whale watching companies on Cape Cod. We took a tour with them a few years ago and saw lots of whales and dolphins — an unforgettable family experience!

⭐️ Play at the Cape Codder Water Park: This large indoor/outdoor park has a variety of activities for kids, including four water slides, a wave pool, and a “stormy river” with waterfalls, rapids and a spouting humpback whale.

⭐️ Parasail or jet ski along Cape Cod Bay: Book sessions through Dennis Parasail and Jet Ski for a thrilling and unforgettable Cape Cod experience.

6. Salem

Salem is well-known for its superstitious past and is especially popular in the fall around Halloween, when you’ll see thousands of people walking in costume around town. But Salem is just as worth seeing in the warm summer months (and you’ll likely experience fewer crowds).

⛴ To make a day trip to Salem even more exciting for kids, consider taking a fast ferry from Boston via Boston Harbor Cruises.

Family Fun Things To Do

⭐️ Visit the Salem Witch Museum: If you have older kids, it might be worth touring the Salem Witch Museum to learn about the infamous Salem Witch Trials of 1692.

⭐️ Take a Salem Walking Tour: Learn even more about the mysterious history of Salem through this popular, 5-star-rated walking tour.

⭐️ Tour the Peabody Essex Museum: Experience the oldest continuously operating museum in the United States, open since 1799. You’ll find dinosaur fossils, fashion items, Asian and maritime art, and lots more.

⭐️ Play at Salem Willows Park: This seaside park has great picnic areas and ocean views, but the biggest draw for kids is likely the video arcade and popcorn on site.

⭐️ Lunch and bowl: American Flatbread has its own bowling alley inside, so your family can order delicious wood-fired pizza followed by a competitive game or two…or three!

7. Mini road trip through the Berkshires

People gravitate toward Boston and the North Shore, especially in the warm summer months, but the Berkshires region on the west side of the state would make for a fun family day trip in Massachusetts as well.

For this day trip, I recommend hopping from one small town in the Berkshires to the next, catching a highlight activity in each place. It’s fun to take a road trip for a week or more, but if all you have is one day, a mini road trip can still feel like an adventure!

🍁 The best time to visit the Berkshires is from mid-September until early October. It’s one of the best places in New England to see the beautiful fall foliage! 🍁

Family Fun Things To Do

Start your road trip in Lenox and work your way south through Lee, South Egremont, and Stockbridge before ending in Great Barrington. Below are key things to do at each stop:

⭐️ See a Tanglewood concert: Located in Lenox, Tanglewood is the summer home of the Boston Symphony Orchestra. If your family loves music, this is a great chance to see a world-class performance in a small town.

🦅 Note: Tanglewood performances only run in the summer, so if you are planning a fall day trip to the Berkshires, you could consider a visit to the Mass Audobon instead, where your family can go hiking, bird watching, or even volunteer together.

⭐️ Hike part of the Appalachian Trail: Located in Lee, October Mountain State Forest is Massachusetts’ largest state forest. The 5.9-mile hike to Finerty Pond is part of the Appalachian Trail. The entire hike takes around three hours to complete, but you could walk just a portion of it as well.

⭐️ Climb and zipline: Catamount Aerial Adventure Park is in South Egremont close to the New York border and features 9 different aerial trails with more than 150 different challenges.

⭐️ Visit the Norman Rockwell Museum: See the artwork of this iconic American painter in the historic town of Stockbridge. The museum often hosts family-friendly events with stories, crafts, and more. Pop over to Main Street Cafe for lunch afterward.

⭐️ Finish with a hike or show: Depending on your energy levels by this point, you can choose to either hike at Monument Mountain Reservation or see a show at the historic Mahaiwe Performing Arts Center in Great Barrington.

Family Day Trips in Massachusetts: Winter & Spring

Here are my top recommendations for family day trips in the winter and spring:

8. Boston

People rave about Boston in the fall, but my favorite time to see the city is actually in the spring when the trees are in full bloom and the town comes alive after a long, cold winter.

There is a never-ending list of things to do in Boston, including plenty of activities for kids. We’ve lived here for well over a year now and are still constantly finding new places to take our daughter.

Family Fun Things To Do

⭐️ Explore Boston Common and the Boston Public Garden: These historic parks are right next to each other and are great places to let kids run around without worrying about cars. The Boston Common includes the Frog Pond, which turns into an ice rink in the winter!

⭐️ Tour the city on a duck boat: The iconic Boston Duck Tours are a unique way for families to learn about the city. These “amphibious” vehicles can ride on both land and water, so your tour will include views from within the city and from the vantage point of the Charles River.

⭐️ Eat authentic Italian food in North End: North End is known as Boston’s Little Italy and is the perfect place to stop for lunch or dinner. I recommend pizza from Regina’s Pizzeria on Thacher Street, followed by the most delicious cannolis from Mike’s Pastry on Hanover Street.

Note: Be sure to bring cash as a lot of places in North End are cash-only!

⭐️ Visit the Museum of Science: Our daughter had a blast here. There are lots of interactive, themed exhibits, including dinosaurs, robotics, and New England wildlife. The museum sometimes even hosts special activities for kids to enjoy during part of the day. When we went, they had a trampoline building contest.

⭐️ Go on a Freedom Trail scavenger hunt: The Freedom Trail is one of the best ways to tour Boston by foot and see 16 key historic sites that played a role in the Revolutionary War.

You could make the Freedom Trail more entertaining for kids by asking them to search for key details at each site (like Paul Revere’s gravestone at the Old Granary Burying Ground or the angels on the organ at Old North Church).

9. Lexington & Concord

Lexington and Concord were made famous for their role in the American Revolution, but these neighboring towns also have a literary history and plenty of natural beauty to enjoy during a family day trip.

Family Fun Things To Do

⭐️ Hike around Walden Pond: Visit the place that inspired author Henry David Thoreau to write his famous novel Walden. Walk the 1.7-mile trail around the pond and finish off with a refreshing swim. Along the trail, you’ll also come across the former site of Thoreau’s log cabin.

⭐️ Visit Minute Man National Historical Park: Learn about the Battles of Lexington and Concord — the “shot heard round the world” — that started the American Revolution at this national park in nearby Lincoln. Follow the Battle Road Trail and see the famous Old North Bridge.

⭐️ Canoe or kayak down the Concord River: Rent boats from the South Bridge Boathouse and navigate your way along the Concord River to see Old North Bridge and other historic sites.

⭐️ Experience a working farm: Verrill Farm hosts lots of family-friendly events in the summer, including kids cooking classes, a strawberry festival, and pancake breakfasts.

⭐️ See an interactive show at Playtime Theater: Concord Youth Theatre actors perform familiar children’s stories throughout the winter and spring, complete with sing-a-longs. These shows are best for ages 2-9, and tickets are $5 at the door (no advance sales).

10. Northampton

Northampton is a popular town in western Massachusetts filled with artistic and interactive attractions for the whole family.

Family Fun Things To Do

⭐️ Check out the Northampton Ice Art Festival: In January each year, artists spend a day carving sculptures that are then put on display in the city — come marvel at the amazing creativity!

⭐️ Explore the Eric Carle Museum: This museum, located just a few miles outside of Northampton, is devoted to children’s picture book art and has a variety of special exhibits every year targeted to families.

⭐️ Bike the Norwottuck Rail Trail: Ride along the scenic, 11-mile paved trail that used to be the Boston and Maine Railroad.

⭐️ Race each other on go karts: Just a few miles outside of Northampton is Pioneer Valley Indoor Karting, an indoor go kart track that will put your racing skills to the test!

⭐️ Go sledding at Hospital Hill: This popular hill has different levels of steepness for both beginner and experienced sledders.

11. Great Barrington

I mentioned Great Barrington as a stop during a mini road trip through the Berkshires in the Summer/Fall list, but it’s worth spending an entire day here in the winter for some fun in the snow.

Family Fun Things To Do

⭐️ Butternut Ski Area and Tubing Center: This is one of the most popular ski resorts in Massachusetts. They’ve been in operation since 1962 and have the motto, “Where families go to play in the snow.” Enjoy 22 different ski trails and a snow tubing hill!

⭐️ Go snow hiking at Monument Mountain: Strap on some good snow boots and enjoy a wintery hike at Monument Mountain Reservation.

⭐️ Grab delicious brunch from GB Eats: Enjoy breakfast all day or a variety of other menu items, including a mouthwatering cider milkshake. This is a favorite restaurant for Butternut Ski visitors.

⭐️ See a show at the Mahaiwe Performing Arts Center: After a long day of playing in the snow, relax while watching a movie or live performance at this historic theatre. They often feature family-friendly shows.

12. Marblehead

For a small-town family day trip experience, visit the quaint seaside town of Marblehead just 16 miles north of Boston. This is a great choice if you’re looking for a quieter day out.

Family Fun Things To Do

⭐️ Climb the rocks at Castle Rock Park: This is Marblehead’s hidden gem. The entrance to the park is easy to miss, but once you walk inside, you’ll be greeted by the most majestic ocean views. Kids will love climbing the giant rock formation that’s right on the coast.

⭐️ Enjoy lunch at Shubie’s Marketplace: After you’ve had your fix of rock climbing at Castle Rock Park, head over to Shubie’s for fresh sandwiches and cannolis.

⭐️ Explore Mud Puddle Toys: I stumbled across this toy store the last time I was in town, and they have the most fun assortment of games and activities to choose from. If you don’t mind giving your kids some temptation, this is a fun stop to make during your day in Marblehead.

⭐️ Watch the sunset at Chandler Hovey Park: This grassy park is known for its excellent sunsets and is a great way to finish off your day in Marblehead. Be sure to walk to Marblehead Lighthouse while you’re there.

13. Worcester

Worcester is Massachusetts’ second-largest city and about an hour west of Boston. If you’re looking for an urban day trip with your family but Boston feels too overwhelming, Worcester is a nice alternative option.

Family Fun Things To Do

⭐️ Try the Central Rock Gym: Escape the cold and enjoy this indoor rock climbing gym, which includes lead climbing, top roping, bouldering, fitness, and yoga.

⭐️ Walk through the New England Botanic Garden: If visiting Worcester in the spring, explore this 171-acre botanic garden just eight miles north of the city. They host special activities for kids and families, including the self-guided “Love Letters to the Garden,” “Spring Story Walk,” and “Beats & Blooms: Spring Sing-A-Long.”

⭐️ Explore the EcoTarium: Check out this science and nature museum with interactive exhibits for all ages, including live animal habitats and nature trails.

⭐️ Try an Escape Room: There’s nothing like a little healthy tension to bond as a family. 😉 Try one of the four different escape rooms at Escape Games Worcester: Dreamscape, Fallout, Conspiracy, and Museum.

⭐️ Go sledding: There are several great places to go sledding in Worcester, including Quinsigamond State Park, Holy Cross College, and Green Hill Park.

BONUS: Day Trips From Boston

If you’re based in or visiting Boston, there are lots of amazing family day trip options within a short driving distance, even outside of Massachusetts. Three of my favorite destinations from Boston are Newport, Rhode Island; Portsmouth, New Hampshire; and Portland, Maine.

✅ Newport, Rhode Island

Newport is only 70 miles (about a 1.5-hour drive) from Boston and is one of New England’s biggest gems. This bustling seaside town is a great place for families to spend a day.

There are numerous shops and restaurants along Thames Street in downtown Newport. The Red Parrot restaurant has a large menu with a variety of options to satisfy different palates (you know, for those picky eaters ;)).

Kids will likely enjoy the Newport Harbor Shuttle Loop, a hop-on, hop-off water taxi that takes you to several of Newport’s main attractions, including Fort Adams State Park.

The Cliff Walk is another must-do activity in Newport. It’s a 3.5-mile trail right along the ocean — a great place for your kids to release some energy before touring one of the historic Newport mansions, like the Breakers.

🎧 To keep your kids entertained inside the mansion, download the app and bring headphones for each of them so they can listen to the self-guided audio tour.

✅ Portsmouth, New Hampshire

Portsmouth is one of my family’s favorite day trip destinations. It’s only about 63 miles north of Boston and is a great way to escape the big city and have a more small-town feel.

The food is one of the biggest draws of Portsmouth. I highly recommend The Flatbread Company, with their wood-fired pizza made from locally sourced ingredients. Kids often enjoy sitting on the bench by the oven while the chefs make the pizzas.

The Friendly Toast is a great brunch place for families, with its eclectic, vintage interior and fun assortment of kid-friendly meals.

Both restaurants are on Congress Street, one of Portsmouth’s main streets that is filled with boutiques and restaurants.

Once you’re done exploring in town, head over to Jenness Beach or Rye Beach for some fun in the sun.

✅ Portland, Maine

About 112 miles north of Boston (1 hour and 45 minute-drive) is the artsy town of Portland, Maine. This would be a great place for your kids to try their first lobster roll. We really enjoyed High Roller Lobster Co.

Pay a visit to one of the smallest lighthouses, Bug Light, which stands at only 26 feet tall. It’s located at Bug Light Park, a nice coastal park for your kids to let off some steam.

Another fun activity to do in Portland is ride the historic Maine Narrow Gauge Railroad. You also can’t miss a stop by America’s most photographed lighthouse, Portland Head Light, only a few miles outside of Portland.

“The Bug” by Carol Boldt is licensed under CC BY-SA 4.0.

FAQs

Here are answers to a few other frequently asked questions about family travel in Massachusetts and New England as a whole:

What is there to do in New England with a toddler?

So many things! A lot of the activities mentioned in this post would be great to do with toddlers. Here are a few ideas:

Have a beach day

There are plenty of amazing beaches throughout New England.

• Massachusetts: Good Harbor Beach, Coast Guard Beach, and Long Beach
• Connecticut: Silver Sands State Park and Hammonasset Beach State Park
• New Hampshire: Rye Beach and Jenness Beach
• Rhode Island: Narragansett Town Beach and Easton’s Beach
• Maine: Old Orchard Beach and Ogunquit Beach

Visit kid-friendly museums

Here are some of the best museums for kids in New England:

• Massachusetts: Museum of Science and Boston Children’s Museum (both in Boston)
• Connecticut: Kidcity Children’s Museum (Middletown) and The Children’s Museum (West Hartford)
• Maine: Children’s Museum and Theatre of Maine (Portland)

Go to a playground or waterpark

There are lots of great parks in New England for toddlers to enjoy. Some of the best ones in Massachusetts include Constitution Beach (East Boston), Salem Willows Park (Salem), and Cape Codder Water Park (Hyannis).

Is Massachusetts family-friendly?

Yes, Massachusetts is very family-friendly! Hopefully this post gives you a good picture of all there is to do with your family in this state.

Whether you enjoy exploring in nature, relaxing on the beach, touring museums, or playing games, there are plenty of options for a fun family day out.

How do I spend a day in New Hampshire?

New Hampshire is a beautiful state with a variety of things to do with your family. Here are a few ideas:

• Hike or ski in the White Mountains
• Explore downtown Portsmouth and nearby Jenness Beach
• Visit an apple farm or pumpkin patch
• Go kayaking or paddleboarding on Lake Winnipesaukee

Conclusion: Family Day Trips in Massachusetts

There are many great options for family day trips in Massachusetts for every season of the year. Here is a quick recap of the destinations covered in this post:

Summer and fall

• Nantucket: Enjoy some island fun
• Gloucester and Rockport: Neighboring coastal towns with great beaches
• Plymouth: Historic sites from the 1600s
• Cape Cod: Lots of beaches and water activities
• Salem: Mysterious town with a complex history
• The Berkshires: Colorful fall road trip

Winter and spring

• Boston: Exciting and historic city
• Lexington and Concord: Stories of the American Revolution
• Northampton: Artistic and cultural hub
• Great Barrington: Snowy paradise in the Berkshires
• Marblehead: Quiet seaside town
• Worcester: Mid-size city in central Massachusetts

Have fun exploring with your family!