8 Fantastic Family Things to Do in and around Chatham

Are you planning a family trip to Chatham, MA? You’re in the right place! We just returned from a huge family trip to Cape Cod, and we’ve got a great list of fun, family-friendly activities that were proven hits with the adults and the children!

The Chatham Squire

The Chatham Squire is a staple of the area and has been around for decades. If you’re looking for a place to eat where you can let your hair down, look no further. People come from all around the world to the “Squire.” It’s a great place for fresh local seafood, delicious beer, and to meet up with friends and family. An absolute must.

Make sure to get there before the 6pm dinner rush, as it does tend to fill up fast!

Biking the Cape Cod Rail Trail

The Rail Trail bike path is over 20 miles long – but you can bike whichever small sections you want if you aren’t an avid cycler! This pristine path takes you past beautiful bogs and stunning beach scenery. There are tons of different bike shops to rent from in Chatham and nearby towns.

We used Orleans Cycle, because it was directly on the trail, near a free parking lot, and they had great bike trailers to put the kids in! The bikes here were in excellent condition, and you can rent for 2 or 4-hours at a time. Pack a lunch, and make a full day out of it!

Shopping in Chatham on Main Street

The Main Street in Chatham has something for everyone! You’ll find ice cream, candy shops, book sellers, art galleries, souvenirs, clothing boutiques, and lots of interior designs stores. Not to mention, the street is visually beautiful, if you’re looking for that perfect Cape Cod aesthetic!

The Monomoy National Wildlife Refuge

A beautiful, easy hike with children right along the water and only 10 minutes from downtown Chatham. There is a free parking lot with a rangers station just a short walk from the trailhead. The awesome ranger even gave the kids free Cape Cod coloring/activity books! You may spot some horse shoe crabs, seagulls, and even a few seals. We spent about two hours here, and could’ve stayed longer!

The Chatham Shark Center

A wonderful place for kids to visit, especially on a rainy day in Chatham! The staff does an amazing job of teaching you about sharks and the ecological conservation efforts going on. For the kids, there are excellent interactive exhibits, model sharks, and even real shark diving cages! The biggest hit was the interactive tide pool exhibit, where the kids can get their hands sandy! Tickets are $10 per adult, veterans discounts can be applied, and children under 5 are free.

Mini Golf

A classic Cape Cod activity! Have fun and get in on some mini golf action with one of many mini golf centers in and around Chatham. We decided to venture to Bud’s Mini Golf in Harwich Port, MA, but you can find a number of spots even closer to town if you want.

Wellfleet Drive-In Theater

Pile the family in the car and head to the Wellfleet Drive-In Theater. You can go back in time and experience the “good ol’ days” at this nostalgic classic drive-in. They usually present a double feature, so if you’ve got the energy, stick around for the second movie! The first film is always a kid-friendly one.

And if you have littles, get there early to take advantage of the playground behind the concession stand!

Ice Cream

No trip to the Cape is complete without a visit to an ice cream shop. This time, we stopped at Schoolhouse Ice Cream & Yogurt. 10/10, totally delicious with tons of flavors! FYI, they are cash only with an ATM on site.

We hope this list of 8 Fantastic Family Things to Do in and around Chatham has been helpful! Next, check out our VRBO review. This was the perfect place to stay for a large family with kids in Chatham, Massachusetts!