The fall is a beautiful time to explore Cape Cod’s various towns and the greater New England region. If you have any free time over the weekend, consider checking out some of our favorite activities below.
Woods Hole (Falmouth, MA) - A village located on the southwest tip of the town of Falmouth, Woods Hole is home to the Woods Hole Oceanographic Institution (WHOI). WHOI led the joint French-American expedition that discovered the Titanic on the Atlantic seabed in 1985, and visitors can learn more about their underwater archeology, climate research, and ecosystem preservation efforts.
Coonamessett Farm (Falmouth, MA) - Pick your own seasonal produce at this 20-acre farm.
Tree House Brewing Company (Sandwich, MA) - Grab a beer on the beach, just 10 minutes from the Sagamore Bridge after you cross onto the Cape from Boston. Draft beer tickets need to be purchased online in advance. The brewery has a few locations across Massachusetts, so please make sure you’re ordering tickets for the Sandwich location.
Upper-Cape: Bourne, Falmouth, Sandwich & Mashpee
Beach Picnics (Yarmouth or Dennis, MA) - After Labor Day, you can easily find parking at the town beaches and won’t need a resident parking permit. Before heading to the beach, consider ordering pizza from Peterson’s Market or grabbing sandwiches from Dennis Public Market. Information about Yarmouth and Dennis beaches, respectively, can be found here and here.
Swanson(-Nystrom) Cottage (Dennis, MA) - Helena’s maternal grandparents first bought a place on the Cape in the 1960s, and she grew up spending her summers here. If you find yourself in Dennis near Route 6A and looking to grab a glass of wine with Jane and Doug (Helena’s parents), don’t hesitate to reach out!
Canoeing & Kayaking (Dennis, MA) - Rent canoes or kayaks at Cape Cod Waterway. Paddle north to Swan Pond; paddle south to Nantucket Sound. Before picking your direction, you may want to consult the tide schedule.
Cape Cinema (Dennis, MA) - Open since 1930, Cape Cinema is a non-profit art house that features screenings of classic movies, limited run documentaries, and musical performances. The theater’s ceiling was painted by Rockwell Kent, an artist targeted by Senator Joseph McCarthy and ordered to testify before the House Committee on Un-American Activities.
Crowes Pasture Conservation Area (Dennis, MA) - Located under the Dennis Conservation Land Trust, Crowes Pasture includes trails through marshland, forests, and a scenic beach.
Lost Dog Pub (Dennis, MA) - Local noise ordinances require our evening activities to end by 10pm. If you’re looking for a night cap, consider checking out the Lost Dog Pub in East Dennis, which stays open until a respectable 1am.
Cape Cod Rail Trail (Dennis, MA) - This 25-mile bike trail, starting in Dennis and ending in Wellfleet, is paved and family-friendly. Bike rental shops can be found along the way with a quick Google search.
Hyannis Kennedy Legacy Trail (Barnstable, MA) - A village located on the southern shore of Barnstable, Hyannis is home to the Kennedy Compound, where John F. Kennedy, Jr. and his family spent their summers. To learn more about his legacy on the Cape, take a 1.6 mile self-guided walking tour across Hyannis.
Old King’s Highway Historic District (Barnstable, Yarmouth, and Dennis, MA) - Known more commonly as Route 6A, Old King’s Highway winds through the largest historic district in the United States.
Bass Hole Boardwalk (Yarmouth, MA) - Located at Grays Beach, the boardwalk juts out a half-mile across marshland and is a beautiful place to watch a sunset.
Mid-Cape: Barnstable, Yarmouth & Dennis
Brewster Ladies Library (Brewster, MA) - Looking for a public restroom? Google your closest library. The Brewster Ladies Library offers a wonderful option. If you’d like to spend more time on the Cape after this weekend, consider getting a CLAMS Card while you’re at it.
Brewster Flats (Brewster, MA) - The Brewster Flats are the largest tidal flats in North America. Paines Creek Landing (143 Cedar Hill Rd, Brewster) provides you with a parking lot and easy access to the flats. During low tide, you can walk out for about a mile, play in the tide pools, and collect seashells. For information about the timing of low tide, consult the tide charts. It’s especially beautiful during sunset.
Cape Cod Museum of Natural History (Brewster, MA) - The Museum of Natural History offers a handful of family-friendly exhibits—including an aquarium featuring local marine life—and a cute gift shop.
John Wing Trail (Brewster, MA) - This 2-mile walking trail takes you through woodlands, meadow, marshland, dunes, and beach. You can access it from the Museum of Natural History’s parking lot, but if you haven’t paid for museum access before the hike (and don’t want to be scolded) consider parking at Drummer Boy Park (773 Main St, Brewster) and walking over.
Nickerson State Park (Brewster, MA) - If you’ve reviewed the lodging options and haven’t found anything to your liking, you can always camp at Nickerson. Either way, the park offers beautiful hiking trails and access to fresh water ponds. Please, please, please keep an eye out for poison ivy: leaves of three, let them be.
Chatham Bars Inn (Chatham, MA) - Weather permitting, enjoy a drink on the lawn of this 5-star resort overlooking the Atlantic Ocean. From Shore Road, turn west onto Seaview Street, and take the first left into the parking lot where you’ll be greeted by a friendly valet service. Grab a beverage inside from the Sacred Cod’s bar, walk out to the front lawn, and take a seat on one of the Inn’s handful of Adirondack chairs.
Lighthouse Beach (Chatham, MA) - Impacted by the Gulf Stream from the south and the Labrador Current from the north, this ever-changing beach offers beautiful vistas and the opportunity to spot fishing boats and the occasional seal. Parking can be found on Chatham’s Main Street (42 Main St, Chatham) where you’ll be greeted by Chatham Lighthouse.
Chatham Fish Pier (Chatham, MA) - Arrive mid-day and climb up the observation deck to watch fisherman unload their daily catch of lobster, cod, halibut, and dogfish. Seals can frequently be seen competing with you for the first bite.
Marconi Maritime Center (Chatham, MA) - On January 18, 1903, the first two-way wireless communication was transmitted from a Cape Cod beach by Guglielmo Marconi. The message was sent on behalf of President Theodore Roosevelt to Britain’s Kind Edward VII: “In taking advantage of the wonderful triumph of scientific research and ingenuity…I extend on behalf of the American people most cordial greetings and good wishes to you and all the people of the British Empire." Learn more about Marconi and his work on the Cape at the Maritime Center.
Cranberry Bog Tours (Harwich, MA) - Tour an organic cranberry bog around the harvest season, which runs from mid-September to mid-November.
Bell’s Neck Conservation Land (Harwich, MA) - Visit for a 2.75 mile hike and the chance to see bald eagles.
Lower-Cape: Brewster, Harwich & Chatham
Rock Harbor (Orleans, MA) - Visit the site of the War of 1812’s Battle of Rock Harbor, a skirmish between British soldiers and members of the Orleans militia. Consider grabbing a sandwich from JoMama (125 Rte 6A, Orleans) and enjoying it on the Rock Harbor Beach.
Winslow’s Tavern (Wellfleet, MA) - Located in downtown Wellfleet, Winslow’s Tavern is a great option for a lunch or dinner of local produce and seafood. The Swanson-Nystroms are distantly related to the owner, and the restaurant is named after a shared ancestor (the official coffin maker of Plymouth Colony). If the weather is nice, consider sitting out on the front lawn; if raining, consider sitting in the cozy bar on the second floor.
Wellfleet Oyster Fest (Wellfleet, MA) - The Wellfleet Oyster Fest will be taking place on Saturday, October 14 and Sunday, October 15. Learn more about the festival and how to buy tickets here.
National Seashore (Eastham, Wellfleet Truro or Provincetown, MA) - Stretching across 40 miles of beach and marsh, the National Seashore offers access to six different beaches and numerous lighthouses and bike trails.
Kettle Ponds (Wellfleet, MA) - First formed some 15,000 years ago from melting glaciers, the 20 kettle ponds scattered across Wellfleet offer a freshwater option for beachgoers. After Labor Day, you won’t need a resident parking permit, but it will be too cold to swim.
Wellfleet Bay Wildlife Sanctuary (Wellfleet, MA) - Mass Audubon’s Wildlife Sanctuary offers access to 5 miles of beautiful trails; admission tickets cost $8.
Commercial Street (Provincetown, MA) - Known as P-Town, the town of Provincetown has served as a whaling community, an art colony, and a popular LGBTQ+ travel destination. Enter Truro Vineyards (11 Shore Rd, Truro) into your GPS in order to get to Shore Road from the highway (Route 6). Once you get to Shore Road, keep driving north and keep left at the fork when you hit Commercial Street and Bradford Street to stay on Commercial Street. Find free parking on the street or paid parking at MacMillan Pier. Need a podcast for the drive up? Check out Welcome to Provincetown.
The Canteen (Provincetown, MA) - After ordering food and drinks at the front, head to the patio in the back for a beautiful view of Provincetown Harbor.
Dolphin Fleet Whale Watch (Provincetown, MA) - Leave for a 3-4 hour whale watch from MacMillan Pier. In the past, we’ve seen humpback whales, finback whales, minke whales, a blue whale, and lots of dolphins. One time, we were on the boat for 3 hours and saw…absolutely nothing. Dress warmly!
Art’s Dune Tours (Provincetown, MA) - Take a one-hour daytime tour or a two-hour sunset tour of the National Seashore’s sand dunes.
Outer-Cape: Orleans, Eastham, Wellfleet, Truro & Provincetown
Off-Cape: Boston & Greater New England
Freedom Trail & Black Heritage Trail (Boston, MA) - Follow the Freedom Trail’s red brick path for 2.5 miles to learn more about our country’s fight for independence; follow the signs along the Black Heritage Trail for 1.5 miles to learn more about our country’s fight for abolition. The National Park Service has information and audio resources associated with both trails.
Quincy Market (Boston, MA) - If you’re hungry by the time you reach Faneuil Hall on the Freedom Trail, the Quincy Market food hall offers affordable dining options and lots of seating.
Harvard Art Museums (Cambridge, MA) - In June of this year, Harvard announced that their three art museums are now free to all visitors. The main museum entrance sits across the street from Harvard Yard and includes a small cafe if you are looking for a place to sit and enjoy some snacks.
Charles River (Cambridge, MA) - The Head of the Charles Regatta, an annual rowing competition, won’t take place until the next weekend (October 20-22). However, you’ll likely see rowers on the river preparing to compete, and there are plenty of walking paths and benches to take in the view.
The Red House Restaurant (Cambridge, MA) - Located just south of Harvard Square and just north of the Charles River, The Red House Restaurant offers farm-to-table dining with a well-stocked bar and was our date night spot for three years whenever Andrew was in town. If you’re looking for another round, cross the street to Grendel’s Den, a party in a famed 1982 Supreme Court case about religion and liquor licenses (they got the license).
Salem Haunted Happenings (Salem, MA) - The lead-up to Halloween can be a slightly overwhelming—but very fun—time to visit Salem, Massachusetts. For the full month of October, the town hosts Salem Haunted Happenings. If you visit the Salem Witch Museum, you can learn more about Ann Foster, Helena’s 10th-great-grandmother, who was found guilty of witchcraft in a Salem courtroom in 1692.
Leaf Peeping, Cider, and Covered Bridges - If you’re looking for some leaf peeping opportunities (and a road trip), Quechee State Park in Hartford, Vermont and Franconia Ridge Loop in Lincoln, New Hampshire are gorgeous during this time of year. On the drive, keep an eye out for local cideries, covered bridges, and a zebra names Zeus.