The history of Chatham goes way beyond the year it was incorporated (1712, in case you were wondering) with its landscape and salt ponds being created by glacial action during the last Ice Age, creating the beauty you will be exploring during your Cape Cod journey. Offering historical sites, tranquil beaches, and the world-famous Chatham Lighthouse, the time you spend in this town will only get better when you choose Pretty Picky Properties for your vacation accommodations. Reflecting the beauty and charm of Chatham, our homes and cottages will welcome every travelers, creating a safe space filled with all the comforts of home. This guide to things to do in Chatham will show you more about the town and about all you can expect from our Chatham escapes.
Something for Everyone
The appeal of our New England town reaches out to everyone who steps within its city limits, and crossing boundaries that you might not expect from a vacation destination. History is all around as you pose for family pictures at the base of the famous Chatham Lighthouse, constructed in the very early years of the 19th century (1808, to be exact) marvel at the Chatham Windmill, which was once used for grinding corn, and explore the nautical history of Cape Cod at the Chatham Marconi Maritime Center. But Chatham is also a movie making town, its land and seascape having been featured in several movies, including “The Finest Hours” a true story about a famous Coast Guard rescue. And then, on another front, there is the natural side of our Cape Cod hometown, offering warm water beaches, the Monomoy National Wildlife Refuge, and sunsets that will literally take away your ability to speak. A vacation spent in Chatham is destined to be a well rounded one and we’ve listed more of our favorite adventures in more detail in the next paragraphs.
Chatham Railroad Museum, 153 Depot Road, Closed Sundays and Mondays
Traveling by train used to be one of the few ways you could get to Cape Cod after the construction of the railway bridge, but it was more than just a way to get here, train travel was the source of romance and excitement. Today, we tend to drive or fly everywhere, but when you visit the Chatham Railroad Museum, you may find yourself longing for the romance of those long ago days. Housed in a former railway depot, the museum has long been a favored attraction, opening its doors in 1960, and the structure itself was placed on the National Register of Historic Places in 1978. Its impeccably restored 1910 caboose is probably our favorite exhibit of all, allowing visitors to step inside and see for themselves what the romance of train travel was all about.
Families Love Us
In addition to the Chatham Railroad Museum, there is a large amount of Chatham, Cape Cod things to do with families that will appeal to all age groups, activities which include, of course, toes in the sand time. There are many beaches in Chatham in which you can frolic in the surf and build sandcastles at water’s edge, but perhaps the best known one is Lighthouse Beach, lying in the shadow of, yes, you guessed it, the Chatham Lighthouse. It’s white sands are soft and stunning, framing deep blue waters perfectly, and when the sun is setting behind the Chatham Lighthouse, well, we dare you not to fall in love. We’ve listed more family friendly activities below.
AWSC Shark Center Chatham, 235 Orleans Road in North Chatham
Sharks have fascinated us for years and the AWSC Shark Center in Chatham will make your children excited about learning. Offering a selection of water tours that explore the world beneath the waters while educating travelers about sharks and their importance in the earth continuum.
Chatham Candy Manor, 484 Main Street in Chatham, Open Daily 10-6
Do not even try to tell us candy is just for kids, or if you really think that way, we invite you to walk inside the Chatham Candy Manor and spend a little time there. We’re pretty sure it won’t take long to change your mind forever as you scope out all the delicious treats found under its roof, including seasonal collections that offer fun treats such as candies that look like mummies, bats, and pumpkins at Halloween. Featuring small batch fudge that will melt your heart, hand dipped chocolates, truffles, creams, and caramels, and they even offer sugar free sweets that don’t taste sugar free at all.
Chatham Orpheum Theater, 637 Main Street in Chatham
Rainy days and lazy days are always the best times to see a movie and although you can choose to stream movies on our large televisions and stay comfy and cozy as the rain drums down on the roof overhead, the Chatham Orpheum Theater offers fun things to do in Chatham. Offering artsy films and special events, kid’s movies, and classic movies that you will thrill to see on the big screen. Also offering a concession stand that includes pizza, wings, sandwiches, and a host of ice cream treats, honestly, hanging out at the Orpheum is one of our favorite things to do any time of the year.
Cause for Celebration
Just like in your own hometown, the holidays are a time for celebration and the special events listed below celebrate many of the bigger holidays with local celebrations that offer an all-American small town charm and appeal.
4th of July Parade
While parades seem to be disappearing from the national landscape, the Chatham 4th of July Parade is an event we look forward to every year. Offering a different theme each year (in 2024 the theme was Chatham-It’s a Shore Thing!) there will be colorful floats, classic cars, fire trucks, and fishing boats and a vibe of cheer and happiness that will definitely make you feel proud to be an American.
Pumpkin People in the Park at Halloween
Also offering trick-or-treating and costume parties, the Pumpkin People in the Park event is not as spooky as it sounds and is a lot of fun! Chatham has been listed as America’s 4th best town for Halloween and the pumpkins that are made to look like people are one of the top reasons. Kate Gould Park is the “scene of the crime,” and the pumpkins are sure to make you laugh.
Christmas Stroll in Chatham
As you can imagine, Christmas on Cape Cod already looks like a scene straight off a Christmas card, but you may not be able to imagine it gets even better with the Christmas Stroll in Chatham. The shops on Main Street are decorated in colorful lights that shimmer against a blanket of snow that is on the ground, Santa makes an appearance at the fish pier, candy canes are being made, carriage rides are being taken, and of course, people are strolling around in their winter warmest clothes, enjoying every single second of this festival.
Naturally Beautiful
The natural side of Chatham offers its own charms and is guaranteed to make every picture you take appear as if a professional has taken it. It is nearly impossible to take a bad picture outside in Chatham and these outdoor Chatham, Cape Cod things to do will give you a peek into the serene, tranquil, and a little bit of the wild side of our Cape Cod hometown.
Monomoy National Wildlife Refuge, 30 Wikis Way
There are eight different refuges that make up the Eastern Massachusetts National Wildlife Refuge Complex, and the Monomoy National Wildlife Refuge is one of those important eight. Protecting the wildlife that inhabit its nearly 8000 acres, including migratory birds, gray seals, and horseshoe crabs and as you explore its paths and walkways, you will learn just how much each of the creatures are important to the life we lead, even if we can’t see them on a regular basis.
Beachcomber Boat Tours, 174 Crowell Road
Some of the most beautiful parts of Chatham are on the water and Beachcomber Boat Tours let’s travelers explore that part of our world. Offering seal tours along the Chatham Waterways, the Beachcomber is known for its banana color and shape, taking tourists to the places where the seal’s play and the scenery takes their breath away. Private charters are offered and many of the happiest people we have ever met have been married aboard one of the company’s larger boats, witnessed by friends, family, and of course, Beachcomber staff.
Kate Gould Park, 15 Chatham Bars Avenue
A walk in the park, in Kate Gould Park to be more precise, is destined to be a favorite activity, even if you aren’t visiting while the pumpkin people are residing there. Offering a classic gazebo which is where Friday concerts are held in the summer months and all generations of family members dance and sing along to the tunes being played, this park isn’t one you go to have a picnic or to play on a playground, but it is the centerpiece to almost every event that takes place in Chatham, giving visitors a better chance of learning the town a little better.
Follow the Scent of Our Best Restaurants
The best vacations often revolve around the meals we devour and our Chatham restaurants are sure to give you stories to tell, all good ones of course, and the restaurants listed below are a great start to your taste tour of Cape Cod.
Chatham Filling Station, 75 Old Harbor Road
The Chatham Filling Station is not a gas station, it is one of our favorite brunch spots, their brunches are so good they serve it all day! Closed on Wednesdays and Thursdays, the menu is filled with all your favorite breakfast foods, including their Station Breakfast Sandwich and an extensive Benedict section. This wonderful restaurant offers the best way to start your day and can also be a great lunch spot as well.
Wild Goose Tavern, 512 Main Street, Open Daily at 11:30
Speaking of lunch, colorful murals on the walls of the Wild Goose Tavern remind us that life isn’t meant to be serious all the time, especially the one with the geese bellying up to the bar. Offering a little of this, a little of that, and a lot of seafood dishes, the convivial vibe, delicious foods, and creative cocktails will make this eatery one of your favorites and you may even find yourself going back for dinner.
The Chatham Squire, 487 Main Street, Open 11:30 to 1 AM Daily
Whether you are coming to the Chatham Squire for lunch, dinner, or drinks and entertainment, the Chatham Squire will not let you down. Also offering a Sunday brunch, the Squire has been a local tradition since 1958 and if you come all this way and don’t visit the Chatham Squire, can you really feel you have explored all Chatham has to offer? This local hot spot is one we highly recommend at Pretty Picky Properties.
Come Home to Chatham and Our Pretty Picky Properties Retreats
No matter how you fill the minutes of your dream vacation in Chatham, coming home to our Pretty Picky Properties vacation retreats will provide the perfect ending to each beautiful day. Offering all the comforts of home, guests can choose rentals that provide as many as eight bedrooms, giving each traveler their own space to retreat to when the moon is high in the sky and as few as two bedrooms, for those more intimate escapes to the Cape. We pay attention to all the details that make vacation life comfortable and easy and there will be lobster pots in the kitchens, and because we understand the importance of having fun, there may even be game rooms, theater rooms, swimming pools, and hot tubs for your entertainment purposes!
Every Chatham Adventure Begins and Ends with Pretty Picky Properties
Reserve your favorite Chatham retreat today and be prepared to be the envy of all your friends, family, and acquaintances that weren’t able to accompany you on this trip of a lifetime!
