Chatham is the town located on the “elbow” of Cape Cod, and is undoubtedly the most picturesque town on the Cape. While it’s become popular as a shopping and dining destination, there’s also so much more to this adorable little town than just that. So, if you’re looking to fill up your itinerary with all the best things to do in Chatham, MA, then you’re in the right place.
I’ve been traveling to Cape Cod since I was a kid, and it’s one of my favorite places in the entire world to be, so I have so much information about it to share! I’m hoping that this post will help you plan the perfect trip to Chatham, and take advantage of all the lovely things to do do in this picturesque town.
Ready to start planning? Let’s go!
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Is Chatham, MA Worth Visiting?
Yes! If you’re visiting Cape Cod for a day, a weekend or a week or more, Chatham is a great town to visit on Cape Cod. Not only will you see some of the most beautiful houses (bonus points if you visit during hydrangea season in July), you’ll get to see some beautiful beaches, a lighthouse, gorgeous shops, amazing restaurants, and have opportunities for some awesome tours.
Chatham is also a great place to stay during your Cape Cod vacation. The prices tend to be a bit higher for both hotels and vacation rentals, but if it works for your budget, this area is convenient to both the Outer Cape regions, including the Cape Cod National Seashore, as well as the mid-Cape regions.
Best Things To Do In Chatham, MA
Shopping and dining are definitely two things I always come to Chatham for while on Cape Cod, but I also appreciate the natural beauty and charm at every turn. Here are all the best things to do in Chatham, MA to take advantage of everything this little place has to offer.
1. Shop On Main Street
The main attraction is definitely Main Street, and this is one of my favorite things to do in Chatham, MA. It’s packed with gorgeous shops, many of which are independently owned, but there are also some franchise favorites like FatFace and Sundance Clothing. Charming restaurants also line the streets, providing tons of dining opportunities.
Some of my favorite shops to visit in Chatham are:
- The Mayflower: Awesome mix of farmhouse and beachy/rustic homegoods and gifts.
- Fisherman’s Daughter: Amazing little boutique where each apparel item design was created by the owner, and they’re very unique and different from designs in other shops. I’m always inspired when I visit this shop.
- Where The Sidewalk Ends Bookstore: One of my favorite bookstores on Cape Cod.
- The Chatham Home: You’ll be redesigning your beach house in your head from the moment you walk in! So much inspiration here, but also some great gifts.
- Candy Manor: Adorable little candy shop that’s always packed, but worth fighting the crowds for.
Psst! Looking to do some more shopping on your trip? I have a post on the best shopping on Cape Cod, and the best New England gifts to buy for yourself and others, if you need some suggestions on what to look for!
2. Visit Chatham Lighthouse
Another one of the most popular things to do in Chatham, MA is to go see the lighthouse. This lighthouse was originally part of a duo of lighthouses to distinguish themselves from Highland Lighthouse in Truro, which looks very similar. The second lighthouse was eventually pulled from this location, moved and painted red and white, and is now known as Nauset Lighthouse, and Chatham Light still stands here in the original location.
Chatham Lighthouse is one of the few lighthouses in the U.S. that still operates 24 hours a day, so it’s definitely a cool experience to get to see it in person. There is a gate that goes around the lighthouse and the grounds, but you can get a great view of it, and snap some awesome pictures, right from the parking area.
Located about a 1-mile walk from the heart of downtown, you can easily get here on foot, or you can drive. The parking area in front of the lighthouse is the same lot for Lighthouse Beach (more on that, next!), and during the summer months, the 30-minute parking limit is enforced, so plan accordingly. The rest of the year, it’s not really monitored. I always suggest you walk from downtown if you visit on a summer weekend just to make it easier, or get there early in the morning if you want to drive.
Psst! Want to check out some more lighthouses during your trip? I have an entire guide on the best lighthouses on Cape Cod, and tips for visiting them, which is packed with helpful info 😉
3. Explore Chatham Lighthouse Beach
If you go to see the lighthouse, then just turn around, and you’ll see Lighthouse Beach. This is definitely one of the best things to do in Chatham, MA, so you don’t want to miss it. Even the views from the parking lot are stunning, but talking a walk on the shoreline here will be even better.
This is also a great place to watch the sunrise. You’ll often find people parking here just before sunrise, and watching it from their car. If you’re an early riser and love a good sunrise on a clear day, this is a great spot to consider visiting.
4. Take A Seal Tour
If you want to head out onto the water and pretty much be guaranteed seal sightings in their natural habitat, then you’ll want to take a seal tour! One of the best ones to check out is Chatham Sport Fishing. They claim to get as close as you can to seals by boat, and from personal experience, I can tell you that this tour is an absolute joy.
You’ll see seals both in the water, and sunbathing out on the beach, and you do get pretty close to them, but also stay at a safe distance. Even without binoculars or a zoom lens, I was able to get a really good look at them. On the tour, you’ll also learn all about the seals, and walk away with a new-found appreciation for this adorable mammal.
Tip: It’s good to know that Chatham Sport Fishing was once Monomoy Island Ferry Tours. Since it’s changed ownership in 2024, I haven’t personally taken the seal tour with them. However, the company has been dedicated to providing the same wonderful seal tours, and I think they’re still absolutely worth checking out!
5. Walk To The Chatham Godfrey Windmill
A short 5-10 minute walk from the heart of downtown through picturesque neighborhood side streets and you’ll find yourself at Godfrey Windmill, which is a really fun thing to do in Chatham, MA. Located in Chase Park, this windmill (technically a wind-powered grist mill) is over 200 years old.
The windmill offers tours inside in July and August, where knowledgeable guides show you how the mill works. During special events throughout the year, the windmill is actually used to demonstrate how it grinds corn. Admission for the tours are free, but donations are suggested.
If you need to drive to the windmill, there is parking available in the park right in front, making it an easy walk up to the mill.
6. Find The Adorable House Replica
Located around 71 Cross Street, one of the coolest things to do in Chatham, MA is to look for the house with the amazing little replica of itself. Confused? Well, just take a look at the photo below.
How cute is this? People walking by sometimes miss this, but I love to scope it out every time I visit. And if you walk to the windmill, you’ll pass right by it.
It’s good to note that this is private property, so please be respectful and don’t trespass, and admire the adorable houses from a distance.
7. See The Seals At Chatham Pier Fish Market
If the seal tour isn’t an option for you, but you’d still like to see some seals, then visiting the Chatham Fish Pier is one of the best things to do in Chatham, MA. Not only is it likely you’ll see some seals, but they also serve up incredible, fresh seafood dishes here.
In fact, this is my top pick for the best and easiest place to see seals on Cape Cod, so it’s definitely worth a visit!
In mid-afternoon, when the fishermen begin to return their boats to the docks with their fresh catches of the day, the seals in the area know, and they follow the boats to the dock and wait for hand-outs. It’s common to see them right at the dock when you visit. It’s not guaranteed, though, and I usually don’t see them when I visit early in the morning (but you may see them sunbathing on the beach nearby!).
The best time to visit is late morning or early afternoon, when all the fishermen start to make their way back for the day. If the seals are hanging out here (which they often are!), you’ll get to see them very up close, and there’s a nice observation deck to admire them for as long as you want.
8. Walk To Stage Harbor Lighthouse
There’s actually another lighthouse in Chatham, so if you love scouting out lighthouses when you travel, this is a really fun thing to do in Chatham, MA. Stage Harbor Light is now privately owned, and you’re not able to walk right up to it, but you are able to get pretty close, and the walk to get there is very scenic.
To get to Stage Harbor Light, you’ll want to park at Hardings Beach, and then take the trail all the way to your left (if facing the water). The trail is about a mile one-way through mostly packed sand, with some spots being softer than others, and follows the coastline of the beach. I recommend taking the sand trail to the lighthouse, and then walking the shoreline back.
9. Grab Lunch At Chatham Bars Inn
For a special dining experience, one of the best things to do in Chatham, MA is to head to the Chatham Bars Inn to dine at one of their restaurants. Known at the top luxury resort in all of Cape Cod, the Chatham Bars Inn has a few options for a memorable outdoor lunch experience (or even dinner!).
For a casual option with classic New England dishes, The Beach House is a great place with outdoor seating on a deck that overlooks Chatham Harbor. For a slightly fancier experience, The Veranda also offers outdoor seating on a deck overlooking the harbor, but has a more elevated menu.
10. Book A Private Clam Bake Experience
In addition to wonderful beachfront dining options, the Chatham Bars Inn also offers private clam bake experiences, which are open to both inn guests and the public.
This dining experience is quite a splurge, but for a memorable group activity, or a special experience, it’s so worth looking into if it fits within your budget!
The CBI clam bake dinner is a completely private dinner that is created just for you and your group, and served right before sunset. Your table will be on the beach, surrounded by tiki torches, and you’ll be served an amazing multi-course meal, where much of it is prepared by the chefs tableside at your own firepit. Get ready for fresh ingredients from the CBI farm, delicious seafood, and also a private bonfire after dinner to enjoy at sunset with all the fixin’s for s’mores on the beach!
This whole experience is especially perfect if you’re planning a romantic celebration like an anniversary or engagement, or if you have a party of up to 8 people.
To book this experience, click here for more information.
11. Admire The Houses Along Shore Road
One of my favorite things to do in Chatham, MA is to take a walk along Shore Road, which is where you’ll find Chatham Bars Inn, as well as other incredible and beautiful homes along the ocean. During hydrangea season in July, many of these homes will have magnificent garden displays with these famous shrubs on display, and you’ll be amazed at how gorgeous the oceanfront homes are.
Tip: If you’re doing this with small children, it’s worth it to note that large sections of Shore Road don’t have a designated sidewalk. There are frequently people walking along the side of the street and drivers are usually careful, but extra caution is needed in some parts, so it’s best to be alert with small children.
12. Learn About Sharks At The Atlantic White Shark Conservancy Center
The Atlantic White Shark Conservancy Center in Chatham is a “jawesome” experience if you’re looking to learn more about these incredible animals. Cape Cod, and Provincetown specifically, are international leaders in marine life education, and here, you’ll learn all about why Great White Sharks are special, and also, misunderstood, with really great, interactive exhibits.
The Conservancy in Chatham is open year-round, but only on certain days of the week, so be sure to click here to check out their hours. There is also a conservancy center in Provincetown, open seasonally, if you’d like to head up to the Outer Cape and visit both locations.
13. Get Pampered At The Chatham Bars Inn Spa
Not only is the Chatham Bars Inn perfect for a special lunch or private clam bake dinner, you can also make a day of it and plan a spa day.
Offering all kinds of treatments to melt your stress away, you can also take advantage of their adults-only swimming pool, zen garden and relaxation room. Pair that with a beautiful lunch or dinner experience after, and you’ve planned a perfect, relaxing day in Chatham.
14. Experience The Chatham Town Band
Every Friday night in July and August, visitors can attend a concert in Kate Gould Park on Main Street, put on by the Chatham Band. Concerts are completely free, making this a wonderful event for families to enjoy together. Pack a picnic, blankets and drinks, and join the local community for a really fun evening in the park.
Musicians in the band all work on a volunteer basis, so if you attend a show during your stay, and really enjoy it, consider making a donation after the show, which helps to keep these performances going.
15. Tour An Oyster Farm
One of the coolest things to do in Chatham, MA is to tour a local oyster farm with the Chatham Shellfish Company. The tour lasts about an hour, and takes you through Oyster River and Oyster Pond, where you’ll learn all about why oyster farming is beneficial for the local ecosystem, and also harvest your own oysters to enjoy at the raw bar at the end of your tour.
Tours run between May and June, and September and October. Sometimes, the company only offers private group tours, so it’s best to reach out to them directly, based on the season, to see what their current offerings are.
16. Get In A Round Of Golf
If you’re an avid golfer, or looking to learn, then one of the best things to do in Chatham, MA is to squeeze in a round at Chatham Seaside Links. Regarded as a wonderful course for both seasoned golfers and beginners and kids, this course is right next door to the Chatham Bars Inn, and provides scenic water views at holes 8 and 9.
The rest of your time, enjoy taking in the salty air breezes, and perfectly-manicured grounds while you enjoy your round. Rental equipment is also available at this course.
17. Bid On Whale Art During Art In The Park
If you fall in love with Chatham as much as I did, then the ultimate souvenir would be a piece from Art in the Park. Each summer season in Kate Gould Park (the same park at the Chatham Band Concerts!), you’ll find whale or shark-themed artwork on display, and visitors are able to bid on each piece to purchase.
Each piece is made by a local artist, and has its own theme. Proceeds from sales go to the Chatham Merchants Association, which reinvests the earning back into the town, making improvements for locals and visitors alike. So really, with a bid, you’re just believing in the town’s future, which is an awesome community project to take part in.
Art in the Park runs from late-June through mid- to late-August. Each year the starting and ending time differs, so be sure to check out social media for the official season each year during your visit.
Free Things To Do In Chatham, MA
The great thing about visiting Chatham is that there are tons of free things to do for the whole family. Below is a list of free things to do in Chatham, MA:
- Godfrey Windmill
- Walking Shore Road
- Seeing Seals at the Chatham Fish Pier
- Exploring Main Street
- Walking through Chatham’s beautiful side streets
- Visiting Chatham Lighthouse
- Visiting Chatham Lighthouse Beach
- Chatham Town Band Concerts in season
- Visiting Art in the Park in season
- Walk to Stage Harbor Lighthouse (parking fees may apply in season if you don’t have a beach parking sticker)
How Do I Spend A Day In Chatham?
Chatham is a great destination if you only have a few hours, or are looking to spend the entire day. For a full-day itinerary, here’s what I suggest after countless visits to Chatham myself:
Morning: If you’re an early riser, catch the sunrise at Chatham Lighthouse Beach. Even if you don’t get there for sunrise, definitely hop on over here in the morning to start your day at the lighthouse and then the beautiful Chatham Lighthouse Beach.
Afternoon: Explore the shops on Main Street, walk to the windmill, and come back to Main Street for lunch. If you want to have a nice lunch at Chatham Bars Inn, you can walk there from Main Street, and combine that with a walk on Shore Road, since that’s where the hotel is. If you stay on Main Street, I would do lunch first, and then head over to Shore Road after.
Early Evening: If you haven’t already, head over to Shore Road to walk and admire the houses. The Chatham Fish Pier is also in this area, so combining these two is a great idea. Then drive over to either Hardings Beach or Ridgevale Beach, and take a walk closer to sunset along the shoreline. Hardings Beach is where Stage Harbor Lighthouse is, so that is also an option. Towns typically stop checking for beach parking stickers after 4-5p.
Evening: End your day in Chatham with a lovely dinner at your pick of any of the amazing restaurants in town! See below for a few of my favorites.
Does Chatham Have A Downtown?
Yes! In fact, Chatham has one of the most prominent downtowns in all of Cape Cod. Main Street is the center of Chatham’s downtown, and home to most of the shops and many of the restaurants. It’s easy to navigate and walk around, and you can spend hours just on Main Street alone. There are also plenty of side streets to explore, and even a park in the center of downtown called Kate Gould Park.
Things To Do In Chatham, MA In The Winter
Because Chatham has a very distinct downtown feel, it makes it a great place for a New England winter getaway. The Chatham Bars Inn is open year-round, and a great place for a winter day of pampering at the spa, and a fireside meal at their tavern.
In the winter, you can also walk up and down Main Street to visit the shops that are open year-round, and grab lunch for a cozy afternoon of shopping. You can also head over to Godfrey Windmill in the winter, and hope that there will be a dusting of snow that will make it even more magical to see.
Having been to Chatham in the winter myself, I even loved walking on the beaches in the dead of winter. On a calm day, Chatham Lighthouse Beach was delightful for a winter walk along the beach. This beach tends to have calm winds most days, anyway, making this a perfect beach for a winter walk.
Where To Park In Chatham, MA
The great thing about parking in Chatham is that most of the parking is free. The downside to parking in Chatham in peak summer season is that it can be a bit challenging. For that reason, I recommend you start your day in Chatham as early as possible, park close to Main Street, and just walk everywhere.
The best place to park in Chatham is right on Main Street. These will be spots where you’ll parallel park, and I always suggest you just take the first spot you see. While Main Street is long, it’s very manageable, and you’ll end up walking up and down the whole thing, anyway.
There are also a few public parking lots just off Main Street, and these can be found at:
- Kate Gould Park (entrance on Chatham Bars Avenue)
- Main Street/Cross Street Lots (there are two lots in the same area here)
- Community Center Lot (enter/exit on Main Street)
- Stage Harbor Road (enter/exit along Stage Harbor Rd, near main Street)
Between Main Street and these lots, you should have no problem finding parking, even on a busy summer weekend. I often visit Chatham on a Saturday or Sunday in July and August, and always find a spot right on Main Street when I arrive between 9-10:30a.
Best Beaches In Chatham, MA
While I’ve already mentioned Chatham Lighthouse Beach, another wonderful things to do in Chatham, MA is to explore the other beaches. Here are some of my other favorites in Chatham:
Ridgevale Beach in Chatham is a gorgeous beach which starts with a footbridge that leads you to the shoreline. This is a great place to spend just a few hours for a scenic walk, or even the whole day for swimming and picnicking. There are also snack shacks and lifeguards here, making this a great family-friendly beach. Parking fees and/or beach stickers will apply for the parking area in the summer season.
Hardings Beach is where you’ll find the trail to Stage Harbor Lighthouse, but it’s also a beautiful beach to explore. Lined with sand dunes, this beach is also perfect for camping out all day, or for a scenic walk. There are also snack shacks and lifeguards here, making this a great family-friendly beach. Parking fees and/or beach stickers will apply for the parking area in the summer season.
Forest Beach in South Chatham has some beautiful rock jetties you can walk out onto (just be careful, they’re slippery!). This beach is also found along the calm waters of Nantucket Sound, making it a great family beach. Mostly locals visit this beach, and parking is limited. Parking fees and/or beach stickers will apply for the parking area in the summer season.
What Is Chatham, MA Known For?
In the 18th century, Chatham was originally known as a popular fishing and whaling town in the “elbow” of Cape Cod. It also gained notoriety as the home of Monomoy National Wildlife Refuge, a significant part of the Eastern Massachusetts ecosystem, as well as Chatham Lighthouse, which was first erected in 1808 by President Jefferson.
Present Day, Chatham, MA is known as being an affluent resort community on Cape Cod, with average housing prices in the millions. Notable celebrities such as Harry Connick Jr. have also owned houses in Chatham.
Best Restaurants In Chatham, MA
There are seemingly endless restaurant options in Chatham, so if you’re overwhelmed by where to eat, let me steer you in the right direction! This list excludes the Chatham Bars Inn and Chatham Fisher Pier, since we’ve already covered those.
The Chatham Squire: A great little tavern perfect for a casual, New England meal. I love coming here for lunch, especially on a rainy day. They have a great lobster roll, here, too.
Impudent Oyster: A really great place for local oysters (or really, any fresh seafood catches), with a homey, relaxed atmosphere that also feels slightly more upscale.
Wild Goose Tavern: The perfect spot for an al fresco lunch or dinner right on Main Street. Slightly upscale for lunch, a bit fancier for dinner.
Del Mar Bar & Bistro: A wonderful date night spot with amazing food. The focus is on seafood, but they also do pizzas, and the atmosphere is very romantic and cozy. They also have great desserts!
Where To Stay In Chatham
The Chatham Bars Inn: For a luxury stay right at the beach, you’ll want to check out the Chatham Bars Inn. With a spa and amazing restaurants on-site, walkability to town, and cabanas on the beach right across the street, this is the ultimate place to stay for pampering and relaxation.
Click here to check rates & availability at the Chatham Bars Inn
The Hawthorne: Perfect for a beachfront hotel getaway that won’t cost as much as the Chatham Bars Inn. Located right on the beach, and also walkable to Main Street’s shops and restaurants.
Click here to check rates & availability at The Hawthorne in Chatham
The Greyfinch: Perfect for a slightly more affordable option in recently renovated rooms that’s still an easy walk to Main Street’s shops and restaurants.
Click here to check rates & availability at The Greyfinch
You may also find these posts helpful:
- Best Time To Visit Cape Cod
- Best Towns To Stay In On Cape Cod
- Ultimate List Of The Best Things To Do On Cape Cod
- Best Lobster Rolls On Cape Cod
- Best Sunsets On Cape Cod
- Best Things To Do On Cape Cod For Adults
- Best Waterfront Restaurants On Cape Cod
- Summer In New England: Best Places To Go & Things To Do!
- Best Beach Towns In New England
- Best Places To See Seals On Cape Cod
- Christmas On Cape Cod: All The Best Things To Do
- Ultimate Guide To The Cape Cod National Seashore Beaches
And here are some more Cape Cod town guides you may enjoy:
- Best Things To Do In Wellfleet, MA
- Best Things To Do In Harwich, MA
- Best Things To Do In Dennis, MA
- Best Things To Do In Falmouth, MA
- Best Things To Do In Brewster, MA
- Best Things To Do In Provincetown, MA
- Best Things To Do In Sandwich, MA
- Best Things To Do In Eastham, MA
- Best Things To Do In Orleans, MA
That’s A Wrap On The Best Things To Do In Chatham, MA
And there you have it! All the very best things to do in Chatham, MA to help you plan the perfect day, or week-long vacation. Whether you’re looking to just come for an afternoon of hitting up the shops, or you’re looking to also enjoy the local beaches and take in the nature beauty, Chatham really does have it all, and it one of my favorite towns on Cape Cod to visit for that reason.
