The Chatham Squire has been an iconic Cape Cod establishment since 1968. The full menu is served on both the restaurant and tavern sides, with live music on the tavern side every night except Trivia Tuesdays. It's open from lunch until closing time. If you want a quieter meal and a chat with the bartender, try a sunny beach day or the window between 3 and 5 PM! Check out Main Street Chatham on your way in -- there are tons of bookstores, boutiques, gift shops, ice cream places, and candy stores!
Try a lobster roll or fish sandwich right on the pier for lunch, watch the fishing boasts come and go, and see the harbor seals swarm for fish scraps, then pick up some fresh local fish for dinner from the marketplace!
Need lunch and a beer? Can't miss the game, any game? Need a before dinner drink? An after dinner drink? Check out the Hot Stove Saloon, a cozy and lively sports pub in the center of Harwichport. It's walking distance from the wedding, several recommended hotels, and Bank Street Beach.
Famous for its souvenir sweatshirts, the Beachcomber is a bar and club located on a dune above Cahoon Hollow Beach in Wellfleet. It's also the opening set of another Sullivan love story; Isabelle's parents started dating after reconnecting one night at the Beachcomber. Go back and forth between the beach and the bar all day, or bring coolers down to the beach for the day and head back up to the Beachcomber at happy hour for oysters, fried clams, and any drink your heart desires. Plan to get there very early if you want to park nearby -- otherwise be prepared to park a mile away and take a bus!
One of Harwichport's nicest public beaches, Bank Street Beach is fully life-guarded during daytime hours, has washrooms, and is walking distance from downtown and several of the suggested hotels. Because it is in Nantucket Sound, the water is warmer and the currents are gentler than beaches facing the open ocean!
Attention, dog owners! Most beaches on the Cape are closed to dogs during the summer, but Nauset Light Beach allows you to explore the seaside with your leashed canine companion. Make sure to give any roped-off piping plover nesting grounds a wide berth. This open-ocean beach has colder water with stronger currents, but is open to swimming and offers some of the best boogie boarding on the Cape. Enjoy the open ocean but be smart about it: check for the shark warning flag on the lifeguard stand, stay close to shore, and stay in lifeguarded areas.
The Cape Cod National Seashore is forty gorgeous miles of beaches, marshes, woods, bogs, and dunes stretching along the Outer Cape. Hike along the dunes or beaches in the footsteps of Henry David Thoreau, try surfing in the rougher waves of the open ocean, or watch the sun rise over the Atlantic!
Sundae School is the best ice cream place in Harwichport, offering delicious local flavors like Bass River Mud, all the classics, and dairy-free sorbet options. It's walking distance from the wedding and several recommended hotels. Sundae School is also the origin point of another Sullivan love story!
Explore Main Street Chatham and all it's boutiques and restaurants -- once you've gotten a parking spot, you'll want to take full advantage of it! Don't misss the Chatham Candy Manor. It's THE place to get fudge, penny candy, saltwater taffy, and chocolate in the shape of every sea animal you can imagine.
Located on the tip of Cape Cod, Provincetown has been a vacation hotspot for the queer community for decades, and the 47th annual Carnival Week runs from August 17-23, 2025, right before the wedding! Check out the Carnival Parade on August 21 (this year's theme is Summer Camp), or go any day all week to enjoy the food, art, costumes, bars, and entertainers! Provincetown is about an hour drive or a two hour bus ride from Harwichport.
These bike paths run along railroad routes that went out of service in the 1960s. The Old Colony Rail Trail runs through Harwich and Chatham, with entrances less than a mile from the wedding! It connects to the Cape Cod Rail Trail, which is 25 miles long and extends all the way to Wellfleet.
Want to get out on the water while you're here without going too far? Try a cruise along the shores of Harwichport and Chatham. Check out the boats, lighthouses, and landscapes of some of the most most beautiful harbors in America. These cruises take place entirely within Nantucket Sound, and mostly within harbors, where the water tends to be quite flat. Depending on the time of day, they offer ice cream and/or cocktails!
For a further-from-shore but still local adventure on the water, motor out to Monomoy, a barrier island between Chatham and the Atlantic and home to large groups of seals. These tours launch from Saquatucket Harbor and visit Wychmere and Stage Harbors en route to Monomoy. The scenic excursions passes gorgeous protected wildlife areas, some of the most spectacular houses on the Cape, and the iconic Chatham Light.
A more extensive ocean voyage, Dolphin Fleet Whale Watches launch out of Provincetown and head out past Race Point, the tip of Cape Cod, to deeper water in the Atlantic. They are extremely reliable and guarantee whale sightings. We can personally vouch for this - we've seen whales, and a lot of them, every time! Naturalists who are familiar with many of the local whales guide each excursion and collect data for conservationists and marine life researchers. The boats serve drinks and snacks, and have indoor and outdoor areas. Provincetown is about an hour drive or a two hour bus ride from Harwichport. These whale watches are truly unbelieveable. You can get within ten yards of pods of whales, watch them spout, dive, work together to hunt, and maybe even jump if you're lucky!