17 Serendipitous Things To Do In Chatham MA For Lovebirds

WHY GO: There are both wild and tame things to do in Chatham MA, positioned right at the elbow of Cape Cod where the Atlantic Ocean meets Nantucket Sound. Although now known for its boutique shops and galleries, great restaurants, birdwatching, and beaches, wind whipped Chatham Massachusetts was once the perfect site for wireless telegraph inventor, G. Marconi, to set up his first communication station in 1914.

Mooring and buoy anchors before going into water, Chatham MA

So, explore the history of Chatham from grist mills to telegraphs. Hunt for treasure on beaches of both soft sand and rocks.  Shop local, meet locals, eat, and sleep well on this Chatham MA Getaway.

Start by staying in one of the most romantic places in town.

You’ll find much more to do in other Cape Cod towns on this Dennis to Eastham Getaway Mavens Post. And, in Brewster MA.

Want wilder vibes? Head to Provincetown at the tip of Cape Cod.

Searching for more romantic destinations all over the state? Check out more Romantic Getaways in MA.

Where to Stay in Chatham MA

Exterior of Captains House Inn Chatham MA

Captains House Inn

The Captains House Inn was built for romantic getaways. Literally. The young packet clipper ship Captain, Hiram Harding, built this Greek Revival home in 1839 as a first year anniversary gift to his wife. New owners in 2019 have kept the 1800’s seafaring-captain’s vibe alive.

Furthermore, you’ll be happy to know – if this is your one chance to leave little ones at home for a “Mommy and Daddy” weekend – children under 16 are not allowed.

Parlor seating at captains house inn chatham ma

The Captains House Inn has all the hallmarks of a Select Registry, Four Diamond, Distinctive Inns of New England (DINE) lodging: squeaky clean and beautifully appointed rooms, friendly warm service, hot breakfasts, and an extra something that sets it apart from other hotels.

Tea and breakfast room captains house inn chatham ma

In this case, that “extra something” is  a daily serving of “Cream Tea” – scones and sweet baked treats with clotted cream + tea –  that guests can request at any time during the day.

(One of the best things to do in Chatham MA for non-guests is High Tea from 12-3 – consisting of a three tier platter of sandwiches and baked treats, with tea, for $29pp – $18 for guests. RSVP required).

The Inn is situated close to the water near tony Shore Rd., about a mile from Chatham’s main shopping street and a nice stroll to the Chatham Pier Fish Market.

Captains House Inn foyer Chatham MA

First Impressions of Captains House Inn

Innkeeper, Stephanie, is genuinely warm and funny – with a can-do attentiveness that’s missing in a lot of hotels these days.

Sherry and Port for guests of Captain House Inn

Cozy common areas are festooned with nautical art, ship models, and antiques galore. Carafes of sherry and port sit out on a table for guests in the clubby library. Nothing like a complimentary nip, while playing boardgames, or before bed.

Tradewinds Room Canopy Bed at Captains House Inn Chatham

Guest Rooms at Captains House Inn

There are 16 rooms in total, spread out between three buildings, ranging from 250-700 Sq. Ft. (FYI: all buildings – the captain’s Cottage, Carriage House, and Stables-are within a few yards of each other, so even in inclement weather you can bolt over to breakfast in five seconds).

Each guest room is different – but all redolent of a time when wealthy sea captains brought home eclectic and exotic treasures from around the world.

Soaking tub for two at Captain's House Inn Cape Cod

My room – Tradewinds – features a lace-canopy bed, a soaking tub for two, and a separate shower and toilet room. Furniture runs the gamut from traditional décor to a touch of foreign flair, like a pretty painted French armoire.

Cream, Tea, Scones afternoon at Captains House Inn Cape Cod

Breakfast, Tea, And Welcome Baked Treats

Breakfast and the aforementioned afternoon tea is served in a large solarium. The cookies and scones are phenomenal enough to blast through any dieting willpower. Er, I can attest.

For breakfast, order from a small, yet surprisingly innovative morning meal menu.  Or ask for a custom omelet, if you’d like.

Wedding-Elopement Package

Get hitched, surrounded by your favorite 20 people, for $1,595. The fee includes an officiate to perform the wedding (or elopement), wedding planning, a personal 12″ cake for bride and groom along with bouquet and boutonnière, a celebration champagne toast, a keepsake gift, $75 dinner gift certificate for in-town dining, gourmet breakfast, afternoon tea, late check out at noon, accommodations for wedded couple. Guests must book their own rooms.

Room rates from $235 per night include afternoon tea with baked treats and made to order breakfast.

STAY: More Chatham MA Lodgings

Both The Queen Anne Inn and Old Harbor Inn nearby offer high end stays in historic homes.

If you’ve got deep pockets, consider the Relais & Chateaux Chatham Inn, a swanky contemporary option right in town, or Chatham Bars Inn – on the water.

Pates Restaurant Chatham MA

Chatham has an embarrassment of restaurant riches. Of the dozens here, it’s tough to choose a favorite. But locals consistently point out two: the newer “vegetarian-friendly” Pates, and tried and true Impudent Oyster for innovative American.

Things to do in Chatham MA

Chatham Lighthouse Cape Cod MA

Chatham Lighthouse and Coast Guard Station

Two white lights flash every ten seconds from the Chatham Lighthouse, warning mariners, as far as 24 miles away, off of Chatham’s famously dangerous shoals.

The Chatham Coast Guard is responsible for a good deal of Cape Cod waters, with a history of daring rescues. During a snowstorm on February 18th, 1952, a Coast Guard crew braved impossible conditions to save the lives of 32 men on the Tanker Pendelton, which had broken in two just offshore.

Chatham Lighthouse Beach Cape Cod MA

Chatham Lighthouse Beach

A beautiful place to walk, just be aware that there are an alarming number of stated hazards in and off the waters of Chatham Lighthouse Beach. These include the Jaws-like advisory of Great White Sharks (“do not swim near seals”), plus stinging jellyfish, sand collapse, and rip currents. Swimming conditions can be rough, so keep your children within arms reach.

Monomoy National Wildlife Refuge Chatham MA

Go “Wild” At Monomoy National Wildlife Refuge

When I visited the Monomoy National Wildlife Refuge on Morris Island (accessible by car) in April 2023, volunteers were measuring recent cliff erosion, which seems to be accelerating at a frightening pace. But terns, ospreys, and others don’t care about that – so bring your binoculars and keep on signed trails for some ultimate birdwatching.

Extreme weather has separated parts of the Refuge from Morris Island, creating several barrier islands that include the larger Monomoy Island. With a total 3,500 acres of protected land, Monomoy NWR is ultimately a haven for our fine feathered friends, and a wilderness to us humans.

Godfrey Windmill Chatham MA

Godfrey Windmill

This wind-powered grist mill was built by Colonel Benjamin Godfrey in 1797. The Godfrey Windmill aka, Chatham Windmill, went through a succession of owners until 1957, when it was donated to the town of Chatham and moved to this location. It’s listed on the National Register of Historic Places, and is open for tours on select days in season.

Walking the Labyrinth at Godfrey Windmill Park

Walk the Labyrinth at Godfrey Windmill Park – One of the Most Serene Things to do In Chatham MA

If you have the time, walk the outdoor Labyrinth near the Godfrey Windmill. Meditation like this is good for the soul – and for soulmates.

Beat The Crowd Off Season At Small Neighborhood Beaches

Stage Harbor Beach (private in summer) Chatham MA

Stage Harbor

Come when there’s still a chill in the air, and you just might meet friendly Stage Harbor neighbors checking on their beached small crafts, . But from June-September, don’t even think about scoring a place on the sand here.

Oyster Pond

A saltwater tidal pond (and close to Chatham’s main street), Oyster Pond beach is calm and perfect for little ones. Surrounded mostly by private homes, there are some access points with lovely views.

Cockle Cove Beach

If you are responsible for young kids, you might want to skip Lighthouse Beach on the rough Atlantic Ocean, and head round the bend to the much more tranquil Cockle Cove Beach on Nantucket Sound.

Chatham Pier Fish Market Cape Cod

Buy Right Off the Boat at Chatham Pier Fish Market

Watch the catch come in at the Chatham Pier Fish Market, which is open to the public and a source of fascination (and fresh off the boat fish dinners!) for generations. Visitors are asked to stay away from the working docks and use the Observation Deck, built specifically for tourists. 

Learn Communications History At Chatham Marconi Maritime Center and Marconi/RCA-Wireless Museum

It’s taken millennia to go from smoke signals to the internet, and about 100 years from wireless radio waves to fiber optics. World communication is fascinating, and no better place to learn about its history than Cape Cod, site of the first wireless transmission from Europe to North America.

According to the Chatham Marconi Maritime Center, you can “explore wireless communication technology and its Chatham history, starting with Guglielmo Marconi’s 1914 construction of this site. Dubbed “The World’s Greatest Coastal Station,” the museum building was once home to the largest ship-to-shore radiotelegraph station in the United States. Established in 1921 by the Radio Corporation of America it was known to mariners worldwide as Chatham Radio, WCC.”

Atwood House

Learn about Chatham’s past at the home of the Chatham Historical Society: Atwood Museum.

Chatham Railroad Museum

If you’re into trains, or more specifically, restored “Railroad Gothic” depots, the Chatham Railroad Museum makes for a perfect rainy day hour.

Yankee Ingenuity

If you’ve ever doubted the inventive minds of New Englanders, a characteristic long dubbed “Yankee Ingenuity,” shop at this iconic Chatham store of the same name. From kid’s games to Steampunk skulls (yes, a thing), there’s gotta be something that calls to you here.

Downtown Shops

There’s one Lily Pulitzer store, but most establishments on a long shopping street are independent boutiques.

All articles belong to Getaway Mavens LLC, and all photos belong to us as well, unless otherwise noted. It’s all copyrighted. Please don’t repost anything elsewhere without asking us first. All rights reserved. This site uses cookies to enhance your experience.

We make no guarantees of any price listed on our site. We are not responsible for content on external websites linked to ours, including linked resources, an external blog post, any partner site, hotel property sites, or affiliate sites. We only write about places we have vetted, but can’t guarantee that your experience will be exactly the same.

Posts may contain affiliate links at no cost to you. Several of our trips are also compensated by the respective tourism boards for the city or state we are visiting. This never impacts how we share the destination with you – opinions are always our own and we pride ourselves on that. We do not sell links or accept unsolicited guest posts under any circumstances. Don’t even ask.

United States Copyright, Getaway Mavens, LLC


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

    View all posts