Cape Cod changes completely from one season to the next. Summer brings baseball under the lights and band concerts on the green, fall turns the bogs red with cranberries, winter leaves the beaches to walkers and seals, and spring brings the herring and the first whale watches back to the water. Knowing what each season offers is the key to planning a trip that suits you.
This guide covers the best things to do on Cape Cod through the year: the experiences worth building a trip around, what is on in each season, local picks in Chatham and Harwich, and practical advice on getting around. It is written from Pleasant Bay in Harwich, where Wequassett Resort and Golf Club sits about 10 minutes from Chatham and within easy reach of the Lower and Outer Cape.
TL;DR: Things to Do on Cape Cod
Set along Pleasant Bay, Wequassett offers a starting point for discovering the villages, coastal landscapes and seasonal traditions of the Lower Cape.
- Winter: Explore Chatham’s festive village streets or walk the quiet trails of Bell’s Neck Conservation Lands in Harwich, where marshes and reservoirs offer a peaceful side of the Cape.
- Spring: Visit Stony Brook Grist Mill in Brewster to watch the annual herring run, a seasonal tradition as alewives make their way upstream.
- Summer: Catch the evening light at Rock Harbor in Orleans, where fishing boats and expansive tidal flats reveal a different landscape with every tide, or spend an evening cheering on a Cape Cod Baseball League game.
- Fall: Drive through Harwich and Brewster to see cranberry bogs during harvest season, when the brilliant red berries offer a glimpse into one of the Cape’s longstanding agricultural traditions.
- Day trips: Browse Chatham’s local shops, explore the trails and beaches of Cape Cod National Seashore, or venture to Provincetown for its galleries, independent shops and sweeping dunes. Seasonal ferries from nearby Harwich Port also offer access to Nantucket.
Just beyond the resort, Chatham is approximately 10 minutes away, Orleans 15 minutes and Wellfleet 30 to 35 minutes by car. Wherever the day takes you, keep an eye on the tides, which can transform the Cape’s shoreline within hours.
The Best Things to Do on Cape Cod
Whatever the season, a few experiences sit at the heart of a Cape Cod trip.
Walk the Cape Cod National Seashore
The Cape Cod National Seashore protects the Atlantic shoreline of the Outer Cape and is open year-round. Coast Guard Beach and Nauset Light Beach in Eastham and Marconi Beach in Wellfleet are favorites for long walks, and lifeguards are on duty at six Seashore beaches from late June to Labor Day. Salt Pond Visitor Center in Eastham is the park’s year-round orientation center and a good first stop for trail maps and current conditions.
From mid-May to mid-October, Wequassett guests can also reach the outer beach by boat with Journey to the Outer Beach, a complimentary 15-minute ride across Pleasant Bay with towels, chairs and water provided.
See the Seals
Chatham is one of the best places on the Cape to see seals. Monomoy National Wildlife Refuge is open daily from half an hour before sunrise to half an hour after sunset, and the Morris Island trail gives views across to the refuge’s islands. According to Recreation.gov, hundreds of gray and harbor seals winter along the Monomoy coastline. In the warmer months, seal tours run from Chatham Harbor, including those booked through Wequassett’s on-the-water experiences. Wherever you watch, stay at least 150 feet from the seals.
Visit a Lighthouse
- Chatham Light is an active Coast Guard light station. The overlook across the road from Lighthouse Beach is open year-round, and volunteers run free tours of the grounds on Wednesday afternoons in summer, according to the Chatham Chamber of Commerce.
- Nauset Light in Eastham was built in Chatham in 1877, moved to Eastham in 1923 and moved again, about 300 feet inland, in 1996.
- Wequassett’s lighthouse tours visit Chatham Lighthouse with transport included, for guests aged 12 and over.
Ride the Cape Cod Rail Trail
The Cape Cod Rail Trail is a paved path of about 25 miles through six towns, open from sunrise to sunset. Close to Wequassett, the Old Colony Rail Trail runs about 8 miles between Harwich and Chatham, so you can ride into Chatham for lunch. The concierge can arrange bike rentals and routes through cycling on Cape Cod.
Go Whale Watching
Whale watches leave from MacMillan Pier in Provincetown. The Dolphin Fleet runs from April to October, with trips of 3 to 4 hours led by a naturalist, and sunset whale watches daily from June to September. Closer to the resort, Down Cape Charters runs private whale watches from Wequassett’s dock from June through Columbus Day, with sightings that may include humpback, finback and minke whales. See on-the-water experiences.
Eat Your Way Around the Cape
Lobster rolls, fried clams, oysters and chowder are part of any Cape Cod trip, and every town has its favorites. For ideas, see our guides to the best lobster rolls on Cape Cod and the best restaurants on Cape Cod. At Wequassett, twenty-eight Atlantic, Cape Cod’s only Forbes Five-Star restaurant, serves seasonal New England menus overlooking Pleasant Bay.
Spend Time on the Water
Life on the Lower Cape follows the tides, and some of its best views are found from the water. From Wequassett’s dock, set out on a private sail across Pleasant Bay, join a harbor or seal tour, or explore the shoreline by kayak or paddleboard through our on-the-water experiences. For a different perspective, Cape Cod Harbor Cruise departs from Saquatucket Harbor in Harwich Port for sunset cruises from Memorial Day weekend through mid-October.
Things to Do on Cape Cod by Season
Winter: December to March
Winter reveals a quieter side of Cape Cod, with peaceful marshes, historic village streets and time to discover the places locals return to year-round.
- Discover Harwich’s cranberry country: Take a drive along Bank Street, where working cranberry bogs offer a glimpse into the agricultural heritage that still shapes the Lower Cape.
- Follow historic Route 6A: Drive through Brewster’s historic village to admire former sea captains’ homes, browse antique shops and discover the Cape’s maritime past.
- Find your favorite local coffee shop: Warm up with a freshly brewed coffee in Brewster or Chatham. Visit Snowy Owl Coffee Roasters for locally roasted coffee, or Three Fins Coffee & Cacao Factory in Chatham for espresso and house-made chocolate.
- Discover local culture: Spend an afternoon at the Cape Cod Museum of Art in Dennis or explore the trails at Wellfleet Bay Wildlife Sanctuary.
- Celebrate the holidays: Experience Chatham’s Christmas by the Sea and First Night Chatham, a family-friendly New Year’s Eve tradition featuring fireworks.
- Make the season memorable at Wequassett: Welcome the holidays at the resort’s Tree Lighting Celebration and Merry Market & Fireworks, with festive shopping, seasonal gatherings and fireworks over Pleasant Bay.
For a closer look at the quieter months, explore our guide to winter on Cape Cod.
Spring: March to May
Spring brings the Lower Cape out of its winter rhythm, with village celebrations, blooming gardens and the first signs of the season along the shore. It’s a wonderful time to explore local traditions and discover the Cape before the summer crowds arrive.
- Celebrate Brewster in Bloom: Welcome spring with this annual village festival, featuring local events, a craft fair, family activities and the popular parade.
- Browse local farmers markets: As the season progresses, markets begin returning with fresh produce, baked goods, flowers and finds from Cape Cod growers and makers.
- Explore Chatham in spring: Browse the shops along Main Street, walk the waterfront near the Fish Pier and watch fishing boats come and go as the harbor prepares for another busy season.
- Explore local conservation trails: Wander the wooded paths of Punkhorn Parklands in Brewster, where quiet ponds, pine forests and winding trails offer a peaceful glimpse of the Cape’s natural landscape.
For more seasonal inspiration, explore our guide to things to do on Cape Cod in spring.
Summer: June to August
Summer on Cape Cod is best experienced through the traditions that bring its towns to life: evenings at the ballpark, hydrangeas spilling over garden walls and celebrations along the coast. From Wequassett, the Lower Cape offers plenty to discover beyond the beach.
- Spend an evening at the ballpark: Catch a Cape Cod Baseball League game, where top college players compete in intimate hometown settings. Cheer on the Harwich Mariners at Whitehouse Field or the Chatham Anglers at Veterans Field.
- See Chatham come alive on a summer evening: Bring a blanket to Kate Gould Park for a Chatham Band concert, a longtime local tradition, or browse Main Street before the music begins.
- Follow the hydrangeas: Visit during the Cape Cod Hydrangea Festival in July, when private gardens open their gates and the Cape’s signature blue, pink and white blooms take center stage.
- Spend a morning by the water: Head to the beach early, explore the tidal flats at low tide, or watch fishing boats return to Chatham Fish Pier. Check tide charts before setting out, as the shoreline changes dramatically throughout the day.
- Celebrate summer at Wequassett: Make the most of summer evenings with the resort’s weekly Jazz Festival, running throughout the season into early September, or enjoy live entertainment at Outer Bar overlooking Pleasant Bay.
- Experience a quintessential Fourth of July: Join the crowds along Chatham’s Main Street for its beloved Independence Day parade, when the town fills with decorated floats, marching bands and summer celebration. Then join the festivities at Wequassett’s Fourth of July Gala, a beloved annual celebration that sells out each year.
At Wequassett, summer unfolds along Pleasant Bay, where days on the water give way to sunset sails and dinner overlooking the bay.
For more inspiration, explore Summer on the Bay and our guide to the best beaches on Cape Cod.
Fall: September to November
Fall brings a different rhythm to Cape Cod, from the cranberry harvest and village festivals to crisp days exploring the coast. September often offers warm afternoons and quieter beaches, while October brings harvest celebrations and the first signs of the season changing.
- Discover cranberry country: The harvest typically runs from mid-September through early November. Learn about this longstanding Cape Cod tradition through the Cape Cod Cranberry Growers’ Association.
- Visit a working cranberry bog: Arrange a tour of Hall’s Cape Cod Cranberries in North Harwich, an eighth-generation family farm, through the Wequassett concierge.
- Celebrate at the Harwich Cranberry Arts and Music Festival: This annual September gathering brings together local artisans, live music and community spirit at the Harwich Community Center. The 2027 festival is scheduled for September 18 and 19, with free admission. Visit the festival website for details.
- Make time for fall festivals: Wellfleet OysterFest celebrates the town’s celebrated oyster and shellfish traditions, while Chatham’s Oktoberfest brings seasonal festivities to the village. Check the Wellfleet Chamber of Commerce and Chatham Chamber of Commerce for upcoming dates.
- Explore Cape Cod’s maritime history: Visit the Chatham Marconi Maritime Center to discover the Cape’s role in the history of wireless communication. Check seasonal hours before your visit.
- Take a final boat trip of the season: Early fall offers another opportunity to explore the Outer Beach and see seals before many seasonal boat tours wrap up in October. Confirm tour availability and dates ahead of time.
For more seasonal inspiration, explore the best of Cape Cod in the fall.
Things to Do in Chatham, MA
Chatham sits at the elbow of the Cape, about 10 minutes from Wequassett, and rewards a visit in every season.
Main Street
Stroll along Chatham’s Main Street, where independent boutiques, art galleries and cafés capture the character of this quintessential Cape Cod village. Discover local treasures, browse the toy shop known for its collection of more than 800 varieties of rubber ducks, or pause at Kate Gould Park. On summer Friday evenings, gather beneath the trees for the Chatham Band’s beloved outdoor concerts, a longstanding tradition that brings the community together. In the quieter months, shop hours may be limited, so plan ahead for a leisurely visit.
Chatham Light and Lighthouse Beach
The overlook at Chatham Light looks out over Lighthouse Beach and the Atlantic, and is one of the classic views on Cape Cod. Parking at the overlook is limited to 30 minutes, so it suits a short stop on the way through town.
Chatham Fish Pier
Visit the Chatham Fish Pier on Aunt Lydia’s Cove to see Chatham’s fishing industry in action. Watch local boats unload their daily catch, spot seals gathering below the observation deck, then stop by Chatham Fish Pier Market to indulge in fresh local seafood right on the harbor. It’s a taste of Chatham’s working waterfront and a local favorite worth experiencing.
Monomoy National Wildlife Refuge
Monomoy is open year-round, with trails on Morris Island and seals along the coast. The offshore islands are reached only by boat, and parts of the Morris Island trail are intertidal, so check the tides before you go.
Chatham Marconi Maritime Center
The Chatham Marconi Maritime Center is open on a seasonal schedule, with fall hours from September into October. Adult admission is $14, and children 11 and under visit free.
Chatham Events
- Friday band concerts in Kate Gould Park, July to early September
- The Fourth of July parade on Main Street
- Oktoberfest in October
- Christmas by the Sea, the second weekend of December
- First Night Chatham on New Year’s Eve
Things to Do in Harwich and Harwich Port
Just minutes from Wequassett, Harwich offers a mix of working harbors, quiet nature trails and lively village streets. In summer, Harwich Port comes alive in the evening, as locals and visitors fill the sidewalks, browse the shops and gather for dinner and ice cream.
- Experience Harwich Port after dark: Stroll through the bustling village center on a summer evening, then stop at Sundae School, an iconic local ice cream parlor beloved for its generous scoops and old-fashioned atmosphere. No summer visit to Harwich Port feels complete without a cone.
- Set out from Saquatucket Harbor: Watch boats come and go from this working harbor or head out on a coastal cruise with Cape Cod Harbor Cruise. Seasonal departures typically run from late spring into fall.
- Follow the Old Colony Rail Trail: Walk or cycle this paved trail through Harwich’s wooded landscape, passing quiet neighborhoods and connecting with the wider Cape Cod Rail Trail.
- Discover Bell’s Neck Conservation Lands: Explore trails around freshwater ponds, marshland and the Herring River. Bring binoculars for birdwatching and enjoy a quieter side of the Lower Cape.
- Spend time at Red River Beach: Look out across Nantucket Sound from this stretch of shoreline, a lovely spot for an early morning walk or a sunset visit.
Arts, Culture and Rainy Day Ideas
When the weather turns, spend the day discovering another side of the Lower Cape, from local art and maritime history to independent cinemas and village shops.
- Explore Cape Cod art: Visit the Cape Cod Museum of Art in Dennis for exhibitions featuring artists connected to the region.
- Discover the Cape’s natural history: The Cape Cod Museum of Natural History in Brewster explores the wildlife, salt marshes and coastal habitats that define this part of the Cape.
- Catch a film at the Chatham Orpheum: Settle in at the Chatham Orpheum Theater, an independent nonprofit cinema in the heart of Chatham, for a film in an intimate setting.
- Make time for local shopping: Rainy days are perfect for browsing the independent boutiques, galleries and specialty shops along Chatham’s Main Street or exploring the shops in Harwich Port. Take your time, discover something unexpected and stop for a coffee along the way.
- Enjoy live theater or a classic film: The Cape Playhouse in Dennis brings live theater to the summer season, while the nearby Cape Cinema offers films in a distinctive historic setting.
For more inspiration, explore our guide to Cape Cod arts, music and culture.
Things to Do on Cape Cod With Kids
From exploring tidal pools and spotting seals to cycling shaded trails and spending an afternoon by the water, Cape Cod offers plenty for families to discover together. Visit Chatham Fish Pier to watch fishing boats unload their catch, browse the children’s shops in Harwich Port, or make an evening of ice cream at the beloved Sundae School. At Wequassett, the For the Kids program adds activities for younger guests throughout their stay. For more ideas to plan your time together, explore our guide to a Cape Cod family vacation.
Family-Friendly Shops to Explore
- The Silly Goose, Harwich Port: A cheerful children’s boutique filled with toys, books, games and clothing. A fun stop for little ones to discover something of their own.
- Dr. Gravity’s Kite Shop, Harwich Port: A longtime Cape Cod favorite for kites, toys and beach accessories. Pick out a kite to fly on a breezy afternoon by the shore.
- Ducks in the Window, Chatham: Hundreds of rubber ducks fill the window of this Main Street shop, with styles for every interest and a fun stop for little ones during an afternoon exploring the village.
Day Trips From Cape Cod
Nantucket
Hy-Line Cruises runs a high-speed ferry from Hyannis to Nantucket in about an hour, year-round except Christmas Day. The Steamship Authority also runs a traditional ferry from Hyannis, taking about 2 hours and 15 minutes.
Martha’s Vineyard
The Steamship Authority ferry from Woods Hole to Martha’s Vineyard takes about 45 minutes.
Provincetown
At the tip of the Cape, Provincetown combines whale watches from MacMillan Pier with galleries, shops and the Pilgrim Monument, a 252-foot tower with 116 steps and 60 ramps to the top and views across Cape Cod Bay.
Getting Around Cape Cod
Most visitors explore Cape Cod by car, as many beaches, trailheads and villages sit away from public transport. Distances from Wequassett are short: Chatham is about 10 minutes away, Orleans about 15, Wellfleet about 30 to 35 and Cape Cod Gateway Airport in Hyannis about 30. The resort is about 90 miles from Boston Logan, roughly an hour and a half by car.
Without a car, the Plymouth & Brockton bus links Boston and Logan Airport with Hyannis, and the CapeFLYER train runs from Boston to Hyannis on summer weekends. Wequassett’s concierge can arrange car service, rentals and transfers. See travel to Wequassett.
When to Visit Cape Cod
Every season brings a different side of Cape Cod. Summer is made for beach days, boating on Pleasant Bay and lively village evenings, while September offers warm days, fewer crowds and the beginning of cranberry harvest season. Late spring brings blooming gardens and the return of outdoor activities, while late fall and winter reveal a quieter Cape, with peaceful shoreline walks, local shops and seasonal traditions. For a closer look at what each month has to offer, explore our guide to the best time to visit Cape Cod.
Make Wequassett Your Base
With Wequassett on Pleasant Bay, the best of the Lower and Outer Cape is within reach, and there is always something to return to. Settle in for dinner at twenty-eight Atlantic, take in the changing light across the bay, or unwind in accommodations ranging from waterfront suites and cottages to spacious villas and private homes.
