Things To Do In Chatham MA: Top 15 Most Unique Spots | Stanton House Inn
Fog rolls into the cove while visiting Cape Cod

Chatham, Massachusetts, graces the “elbow” of Cape Cod. It’s famous for fresh seafood, seaside accommodations, and an intriguing shark center. This upscale resort town maintains its New England village charm. With sandy beaches, a lively Main Street, and charming waterfront lodgings, Chatham is ideal for a Cape Cod getaway or a cozy retreat.

Chatham’s appeal comes from its mix of relaxing beaches, quaint shops, and lively local events. You can take a dip in the warm waters of Ridgevale Beach, wander through history on Main Street, and sway to the Chatham Town Band. This guide highlights the best spots to maximize your time in this coastal gem, making Chatham a real Cape Cod treasure.

Ready to explore the best things to do in Chatham MA? Let’s get into it:

Quick hits

  • Chatham’s Highlights: Explore Chatham’s rich history, stunning beaches, lively Main Street, iconic lighthouse, wildlife refuge, outdoor activities and museums.

  • Food & Drink: Savor top restaurants, local craft breweries, and wineries that enhance Chatham’s culinary scene.

  • Nearby Adventures: Visit other unique Cape Cod gems like Provincetown, Martha’s Vineyard, and Nantucket.

 

  Map of attractions, activities, and things to do in Chatham, MA Map design by Stanton House Inn

 

 

 

A Brief History of Chatham, Massachusetts

1894 map of Chatham, Massachusetts, from South Chatham to the Atlantic Ocean

Nestled on Cape Cod, Chatham boasts a rich history of early settlers and native tribes. In 1606, explorer Samuel de Champlain met the Monomoyicks, skilled in farming, hunting, and fishing. The town began as a Constablewick in 1696 and became fully incorporated in 1712, marking the start of its organized governance.

Originally home to the Nauset tribe, particularly the Monomoy people, Chatham thrived after its incorporation. The town expanded in 1797 with the annexation of Strong Island. It became a hub for shipping, fishing, and whaling thanks to its prime location at Cape Cod’s “elbow.” This early prosperity left behind 18th-century buildings that made Chatham one of the top summer getaways in New England.

Established in 1808 by President Thomas Jefferson, Chatham Lighthouse was built to protect passing ships. The original structures were replaced in 1841 with twin brick towers. Over time, erosion took its toll, leading to the northern tower’s relocation to Eastham in 1923, where it became the Nauset Light.

Despite modern changes, Chatham keeps its quaint charm. Main Street, with family-owned shops, eateries, and businesses, maintains a small-town vibe. Even with the summer population swelling to 30,000, Chatham preserves its character. Pedestrian-friendly streets and limited parking enhance its old-world feel.

The Best Things to do in Chatham MA

Chatham brims with activities and sights for all tastes. It plays host to serene beaches to lively Main Street, outdoor adventures and cozy museums. This Cape Cod gem sparkles with attractions around every corner.

Chatham’s Beautiful Beaches

Chatham Lighthouse Beach with calm waters and beach grass on the sand dunes

Think of Cape Cod and you picture perfect beaches, right? Chatham’s shores like Ridgevale Beach are family favorites, where kids can scout tidal pools and grown-ups can soak up the sun or enjoy birdwatching. With handy amenities like snack bars, sailboat rentals, and clean facilities, it’s a breeze to spend a whole day at the beach.

But that’s just a start—there’s more! Check out Hardings Beach to hike to Stage Harbor Lighthouse, or unwind at Forest Beach, a spot loved for its tranquil waters. Lighthouse Beach sprawls in front of Chatham Light on the western side of the elbow. Whether you’re into lounging, swimming, or just gazing at the horizon, Chatham’s beaches are your go-to seaside escape.

Main Street

Main Street in Chatham with shops and galleries in a picturesque town in the summer months

Taking a stroll down Main Street in Chatham is like walking into a living postcard. It’s lined with unique shops and galleries that beg to be explored. Pop into Candy Manor for a sweet treat, or browse specialty items like gourmet oils at Gustare Oils & Vinegars and vintage maps at Maps of Antiquity.

Art lovers will be drawn to The Artful Hand and Chatham Yankee Ingenuity, where local artwork shines. If pottery is your thing, don’t miss Chatham Pottery for beautiful hand-painted pieces. After shopping, grab a bite at one of the local eateries to taste the flavors of Chatham—a perfect wrap to your Main Street adventure.

Chatham Lighthouse and Tours

Chatham Lighthouse with surrounding coastal landscape

Standing guard since 1808, Chatham Lighthouse—or Chatham Light—is a working Coast Guard station focused on search and rescue. Originally one of the ‘Twin Lights,’ it had to be moved in 1877 due to erosion but still lights up the coast every night, visible up to 24 nautical miles away.

Curious about its history? Catch a guided tour during the warmer months, or simply enjoy the breathtaking views from the lighthouse parking area. Close by is Chatham Lighthouse Beach—a spot you can’t miss while in Chatham.

Outdoor Activities in Chatham MA

Boats moored in serene waters of a pleasant bay in Chatham

Chatham is a playground for those who love the great outdoors. Biking through Chatham is a fantastic way to soak up the scenery while getting a bit of exercise. You can pick up a rental bike from Chatham Hood Bikes, which also offers trailers for the little ones, making it a hit for the whole family. For those craving a longer ride, the Cape Cod Rail Trail stretches out for miles, offering a more extensive biking adventure.

Water lovers, you’re in for a treat! Chatham Sailboat Rentals has kayaks and paddleboards ready for you to paddle through:

  • Bucks Creek

  • Nantucket Sound

  • And Taylor’s Pond

Or, why not hop on a seal tour with Monomoy Island Ferry? It’s your ticket to see seals up close and learn about their habitat in a fun, informative way. With Chatham’s picturesque landscapes and peaceful waters, it’s easy to find an outdoor activity that feels like a breath of fresh air.

Monomoy National Wildlife Refuge

One of the diverse habitats at Monomoy National Wildlife Refuge

Spanning 7,604 acres, Monomoy National Wildlife Refuge is a haven for migratory shorebirds and nature enthusiasts. It features diverse habitats like salt and freshwater marshes, dunes, and ponds. It’s also recognized as an Important Bird Area and part of the Western Hemisphere Shorebird Reserve Network. Don’t miss the Morris Island trail for bird, seal, and horseshoe crab sightings. For more wildlife, North and South Monomoy islands are accessible by boat. A must-visit for wildlife lovers and fans of stunning natural scenery.

Cape Cod Baseball League

In Chatham, summer means baseball! The Chatham Anglers, part of the Cape Cod Baseball League, light up Veterans Field with thrilling games that are a highlight for the community. These games aren’t just about sports; they’re about coming together. You can catch a game, grab dinner or drinks, and let the kids loose on the playground—all in one spot, for a perfect, relaxed summer vibe.

This league showcases top college talent, giving fans a sneak peek at future stars. Best of all, you can catch these future big leaguers in action for just a donation at the gate, keeping the spirit of the games open and community-focused. Whether you’re a die-hard sports fan or just looking for a delightful way to spend an evening, watching the Chatham Anglers is a hit.

Scenic Golf Courses

Golf lovers, get ready for some unforgettable rounds in Chatham. The oceanfront Chatham Seaside Links and the sprawling Captain’s Golf Course in Brewster offer both challenging plays and breathtaking views. Opened in 1895, Chatham Seaside Links is especially famous for its stunning ocean vistas that enhance every swing.

No matter your skill level, these courses have something for everyone. Didn’t bring your clubs? No problem! Rental clubs are available, so you can easily join in the fun.

So, swing by, tee off, and soak up Chatham’s beautiful landscapes while enjoying your favorite pastime.

Seal and Shark Encounters

This seal was swimming towards the fishing pier in Chatham, Cape Cod. These grey seals follow the boats in search of a free meal from the day's catch. Remember to never feed the seals!

For wildlife aficionados, Chatham is a dream come true with its close-up encounters with seals and sharks. Head to the Chatham Fish Pier for prime seal watching, especially in the fall when the seals flock to the area, drawn by fishermen’s discarded bait.

For shark enthusiasts, the Chatham Shark Center is a must-visit. The center offers:

  • Educational exhibits on shark conservation and science

  • Insights into the growing population of great white sharks near Monomoy National Wildlife Refuge

  • Stories of legendary sports fisherman Frank Mundus

  • White Shark Expeditions, where you might just spot a great white shark up close

The center both educates and brings you face-to-face with these magnificent marine creatures.

Maritime History and Museums

Chatham’s maritime history shines in its captivating museums. The Atwood House & Museum, dating back to the 1700s, displays the historic Fresnel lens from Chatham Lighthouse among other nautical artifacts. The Chatham Marconi Maritime Center reveals Chatham’s key role in World War II maritime communication, featuring interactive exhibits narrated by Walter Cronkite. The Chatham Railroad Museum offers a glimpse into the town’s past. These museums, with their engaging exhibits, bring Chatham’s rich maritime legacy to life.

The Most Unique Attractions in Chatham, MA

The salt marshes around Chatham, MA, at the elbow of Cape Cod

Chatham isn’t just about sandy toes and tasty seafood; it’s packed with unique spots that beg to be explored. Start with the Chatham Godfrey Windmill in Chase Park. This historic windmill isn’t just for looking pretty—it offers guided tours that delve into Chatham’s past, all while you take in the scenic town views. And don’t miss a stroll through Kate Gould Park, adding a splash of green to your visit.

For music buffs, there’s nothing like a free concert from the Chatham Town Band on Friday nights during the summer. It’s where locals and visitors alike gather under the stars for some toe-tapping tunes. And for movie or live performance enthusiasts, the Chatham Orpheum Theater offers a cozy spot to catch a show in a charming setting.

Whether you’re a history aficionado, art lover, or a cinema fan, Chatham’s unique attractions offer something for everyone.

Restaurants in Chatham, MA

A picnic of fine dining while visiting Chatham

Foodies, rejoice! Chatham dishes out an array of dining options sure to satisfy any palate. Check out these local favorites:

Every meal here promises a culinary adventure. Pair it with a creative cocktail or a local wine for the ultimate dining experience.

Local Breweries and Wineries

Chatham’s craft beer scene is a brew lover’s paradise. Local spots like Hog Island Beer Co., Devil’s Purse, and Jailhouse Tavern serve up unique brews perfect for any beer enthusiast. Tour these breweries to learn about their brewing secrets, try fresh beers, and soak up the local vibe. Whether you’re a beer expert or just enjoy a good pint, Chatham’s breweries offer a perfect way to chill and enjoy.

Seasonal Events and Festivals

Flying a kite and wind surfing at Lighthouse beach

Chatham buzzes with energy during the summer with events and festivals that bring color and excitement to your visit. Art in the Park runs from June through August, featuring local artists and a fun scavenger hunt for art pieces hidden around town.

Don’t miss the Orpheum Theater’s Oscars watch party either. It’s a glamorous night where the community comes together to celebrate Hollywood’s biggest evening.

These seasonal happenings not only spice up your visit but also showcase Chatham’s lively local culture.

Directions to Chatham, MA, from Greenwich, CT

Buoys near fine dining while visiting Chatham

Planning your journey to Chatham from Greenwich, CT? You’ve got options! The simplest and most budget-friendly way is to drive. It’s about a 237-mile trek that takes roughly 4 hours and 30 minutes—perfect for a road trip playlist!

Prefer to leave the driving to someone else? Public transport is your friend. Combine train and bus services via Boston, and you’re looking at around 8 hours and 18 minutes of travel time. If you’re in a hurry, flying from New York’s JFK or La Guardia airports to Hyannis, then catching a bus to Chatham, clocks in at about 6 hours and 51 minutes.

No matter how you travel, getting there is half the fun, especially if you plan on hitting the Old Colony Rail Trail once you arrive!

Hotels, Inns, and Places to Stay in Chatham, Massachusetts

Cute detail of a charming house near the Oyster Pond

After your Chatham adventures, find a cozy spot to unwind. Whether you seek luxury or charm, Chatham’s accommodations offer plenty of options.

Chatham Bars Inn

If luxury is calling your name, Chatham Bars Inn is the answer. Indulge in their world-class spa, complete with a variety of treatments, saunas, and steam showers. Relax by the outdoor pool, unwind in the hot tub, and savor the serenity of their Zen Garden. The spa isn’t the only perk—families love the Kids Crew program. It offers fun activities like birdhouse decorating and sandcastle building.

The Old Harbor Inn

Looking for something a tad more intimate? The Old Harbor Inn offers a cozy stay right near the heart of Chatham’s historic seaside village. Built in 1932 and expertly managed by Ray and Judy Braz since 1996, this beautifully renovated inn delivers top-tier New England hospitality. Whether you’re after a romantic retreat or a peaceful seaside escape, The Old Harbor Inn ensures a delightful stay filled with charm and comfort.

More Nearby Cape Cod Towns and Cities to Explore Near Chatham, Massachusetts

Provincetown is a perfect getaway, or day trip, from Chatham

While Chatham is a gem all on its own, its prime spot on Cape Cod makes it the perfect launchpad for visiting other charming towns and cities nearby. Ready to expand your horizons? Check out these spots:

  • Provincetown: A haven for art lovers.

  • Martha’s Vineyard: Famous for its breathtaking scenery.

  • Nantucket: Packed with unique attractions and a distinct vibe.

Each destination adds a little extra magic to your Cape Cod adventure.

Provincetown, MA

At Cape Cod’s tip, Provincetown boasts over forty miles of beaches, a thriving art scene, and a foodie’s paradise of restaurants, all set against unique architecture. The heart of this lively town is Commercial Street, famous for its eclectic mix of art galleries and quirky shops.

Don’t miss the Pilgrim Monument for breathtaking views, or relax at Race Point Beach. If you’re feeling adventurous, pedal your way through the Province Lands Bike Trail. The best things to do in Provincetown, MA, mix culture, nature, and art into an unforgettable experience.

Martha’s Vineyard, MA

A meal outside in the summer months at one of the best restaurants on Martha's Vineyard

Just a ferry ride from Chatham, Martha’s Vineyard is a picturesque escape with charming towns like Edgartown and Oak Bluffs. You can enjoy everything from sandy beach days and boutique shopping to water sports and cultural excursions.

Looking for more? The list of the best things to do on Martha’s Vineyard has it all—from hiking and biking to fishing and indulgent spa days. With various towns to explore and activities to try, it’s a place where every type of traveler finds their bliss.

Nantucket, Massachusetts

Houses around the sand dunes of a cute town in Nantucket

A short drive and ferry ride away is Nantucket, an island where history meets seaside charm. Forget the car; this island is perfect for walking, with taxis and tours ready to help you explore. Stroll its cobblestone streets, admire historic homes, or relax on pristine beaches. Nantucket is a quaint, picturesque retreat that offers a memorable day out or a peaceful getaway.

Tl;dr

Chatham’s rich history is what keeps this genteel town from feeling like a tourist trap. That said, it’s still a fantastic place to visit, with or without family in tow. Hosting some of the most unique attractions in Cape Cod, as well as some of the best dining, it would be a shame to miss this town on your next visit to the region.

Frequently Asked Questions

When is the best time to visit Chatham?

Summer is the perfect season to visit Chatham. It’s the prime time to soak up the warm weather and dive into all sorts of outdoor fun. Pack your bags and get ready for adventure!

What are some family-friendly activities in Chatham?

Chatham is great for families! You can go biking, kayaking, join a seal tour, or enjoy the Kids Crew program at Chatham Bars Inn. There’s plenty to keep everyone smiling!

Can I see seals in Chatham?

Yes, indeed! Head over to the Chatham Fish Pier, especially in the fall, to see seals frolicking in the water. It’s a fantastic spot for a seal-watching adventure.

Are there any golf courses in Chatham?

Absolutely! Golf enthusiasts can hit the links at Chatham Seaside Links or take a short drive to the Captain’s Golf Course in Brewster. Ready to tee off?

How can I get to Chatham from Greenwich, CT?

Driving is your best bet for getting to Chatham from Greenwich, CT. It’s about a 4-hour and 30-minute ride, covering roughly 381.3 kilometers. Start your playlist and enjoy the journey!

 

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