Cape Cod in the Fall: 15 Things to Do in 2023

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Cape Cod is an ever-popular vacation destination during the summer months, but have you ever heard of Second Summer?

Second Summer is that lovely little period after the summer tourist rush has passed but the early autumn weather is still inviting as all get out for all kinds of fun fall outdoor activities!

There are a ton of great things to do and see in the cool Cape Cod towns, but when the heat and humidity of summer are waning and the cooler days of autumn come rolling in, Cape Cod is the perfect location for a great vacation getaway.

Check out this list of some of the top ways to enjoy Cape Cod in the fall!

Cape Cod in the Fall

Relax in Peace on the Beach

Waves crashing on a rocky beach

A huge advantage of visiting a major tourist destination in the “shoulder season” when most tourists have returned home is that there just aren’t the same crowds to contend with.

In Cape Cod, an autumn afternoon spent lounging at the beach is quieter, calmer, and more peaceful than it is when it is teeming with thick summer crowds.

So pack a picnic lunch and bring your favorite book to decompress in peace by the sea at any one of Cape Cod’s most beautiful beaches, or time your visit to catch some brilliant Cape Cod sunrises and sunsets!


Pick the Perfect Pumpkin at Taylor-Bray Farm

Girl in a red shirt holding a pumpkin while a wagon of pumpkins stands nearby

Taylor-Bray Farm is a historic working farm in Yarmouth Port, right on the edge of the beautiful Black Flats Marsh.

In October they host a Fall Festival with hayrides, farm animals, fresh cider, and pick-your-own-pumpkins, and there is also a Revolutionary War-era farmhouse on the property that has been renovated and housed with period pieces so you can get a peek into what life on this gorgeous farm might’ve looked like centuries ago.

Walk out a bit on the boardwalk to get a better view of the Black Flats Marsh before you leave this lovely historic property.

Read More: 15 Best Pumpkin Patches in Massachusetts


Go on a Whale-Watching Tour

A whale jumping out of the water at sunrise

Whale-watching along the cape is a popular activity from April through October, but one of the best times to see whale activity in this area is in September and early October, when these majestic marine creatures make their annual migration south. There are many fabulous whale-watching tours that depart from the cape, so you’ll have your pick!

Remember to dress warmly as it is always cooler out on the water than it is on shore, and keep your eyes peeled because you’re likely to see other marine wildlife, lighthouses, and other notable local landmarks.

Read Next: 13 Best Hotels on Cape Cod: Where to Stay on the Cape


Attend the Wellfleet OysterFest

Oysters on a blue plate

Wellfleet is one of the best beach towns in MA and is host to one of the most well-known annual Cape festivals, Wellfleet OysterFest.

This mid-October event is a celebration and promotion of the oyster industry that has been such an important part of this town’s success for so long, and you’ll find live music, oyster-shucking competitions, local craft vendors, and lots of great food and drink!

Wellfleet OysterFest is just one of many fun things to do in Wellfleet, so stay awhile and enjoy some of Wellfleet’s beautiful beach scenery.

Read Next: 11 Best Cape Cod Restaurants


Go Apple-Picking at Crow Farm

Little girl with braids smiling and holding an apple next to an apple tree

Picking your own apples is about as quaint and quintessential a fall activity as it gets, and oh, so much fun! Crow Farm in Sandwich suggests following their Facebook page to see when each variety is ripening so you can better plan your apple-picking trip.

Of course, there are so many fun things to see and do in Sandwich that it’s not likely you’ll ever regret making the trip out, even if your favorite varieties of apples aren’t ready to pick yet!


Indulge in a Brew at Cape Cod Brewfest

A group of people standing in front of a booth reading \"CRAFT BEER\"
Editorial credit: TonelsonProductions /

Another fun annual autumn tradition on the Cape, Cape Cod Brew Fest happens in late September, featuring dozens of the best regional craft breweries.

This adults-only event also features live music and local food trucks, with “sampling sessions” that allow you to try out hundreds of different styles of brews while you enjoy the crisp and cool autumn air at this outside Rain or Shine event in East Falmouth. Be sure to bring your thirst!


Tour a Cranberry Bog

A large platform filled with cranberries next to a body of water

Cranberry bog tours are always a cool experience, but fall is the perfect time of year for them as cranberry harvesting season on Cape Cod is from September to December.

If you can catch a tour at harvest time, you might witness the picturesque image of Cape Cod cranberries ready for harvest floating on the surface of the bog, with fall foliage serving as the backdrop. There could even be an opportunity to sample some of the freshly harvested berries for yourself!

Unwind at One of New England’s Favorite Wineries

Closeup of red grapes hanging in a vineyard

Truro Vineyards is one of the most popular wineries in New England, and a visit in the fall will let you enjoy some of its distinctive varietals as the crisp and cool autumn breeze blows in, the leaves on the trees transforming into their ruddy fall colors in the background of this idyllic vineyard.

If you’re less of a vino and more into spirits, South Hollow Spirits is also on the property with their environmentally friendly distilled liquor. Keep an eye on their events calendar to see what to expect on your next visit out.

Embrace Off-Season Rates with a Romantic Luxury Getaway


Red and white lighthouse at sunset

 Visiting Cape Cod in the fall means more bang for your buck as standard rates go down, so if you were putting off that luxury getaway due to price, an autumn stay at a romantic Cape Cod hotel like Chatham Bars Inn might be perfect for you!

One of the most romantic getaway spots in the Bay State, Chatham Bars Inn offers nightly rates in October and November that are a fraction of the price they are during the busiest tourist season, and there are so many awesome things to do in Chatham, too.

Cape Cod is already a romantic vacation destination, now it’s also a (more) budget-friendly one!

Click Here to Check Prices & Book!


Head Out and Hike

A wooden path with hand railings between the trees on a sunny day

Cape Cod has some excellent hiking and walking trails, so take advantage of the cooler fall weather to explore them for yourself in prime comfort.

Venture into the woodlands as the leaves on the trees start their spectacular color show with trails like the Atlantic White Cedar Swamp Trail and the Lawrence Island Wildlife Sanctuary footpaths.

Hiking is a fabulous way to enjoy the stunning natural scenery of the Cape any time of year, but add a little fiery fall foliage into the mix and you’re really set. Nickerson State Park in Brewster sees beautiful fall colors as the leaves change!

Cape Cod National Seashore is an absolute treasure, and as the temps cool slightly, you can spend even more time exploring this gorgeous coastal space. There are lots of great biking trails like the Cape Cod Rail Trail, too!


Take a Lighthouse Harbor Tour

A lighthouse in Cape Cod at Point Gammon
Photo courtesy of Bay Spirit Tours


Available until Columbus Day in October, a Lighthouse Harbor Tour with Bay Spirit Tours offers a great vantage point to see some of the Cape’s loveliest lighthouses and other local points of interest, including the Kennedy Compound in Hyannisport.

As an added bonus, your harbor tour will provide you with some great glimpses of the leaves turning color on the shore, too. Dress in layers, it’s always chillier out on the water!

Attend the Yarmouth Seaside Festival

Every year in early October, the quaint town of Yarmouth puts on a family friendly festival that is the perfect celebration of the cooler weather on the Cape! Spread out over a long weekend, you’ll find a craft fair, beach bonfires, road races, live music, and even fireworks.

The Yarmouth Seaside Festival is a great family friendly event on Cape Cod in fall.


Partake in the Provincetown Food & Wine Festival

A man on a bike and people walking down the street in the evening with scarves; rainbow flags and Confederate flags on the buildings
Editorial credit: Vadim 777 /

In early November, Provincetown holds a 4-day food and wine festival featuring some of this colorful town’s most celebrated chefs and restaurants.

Events include live music, dinners, wine and beer pairing demonstrations, and a champagne drag brunch (Ptown has a great LGBTQ+ friendly vibe!)

Provincetown is full of fun things to do and cool places to stay, so definitely consider staying a day or two at this vibrant town at the tip of the Cape!


Meander through Heritage Museums & Gardens in Sandwich

This gorgeously manicured and expertly landscaped greenspace is a definite must visit if you’re in Cape Cod for early autumn.  Set on 100 picturesque acres, Heritage Museums Gardens in Sandwich is one of the prettiest garden areas on the Cape.

Daily admission is open until mid October, so plan your visit so you won’t miss out!

Go on Cape Cod’s Haunted History Tour

Black and white picture of a mansion on the edge of the water

Leaving from Barnstable, Cape Cod’s Haunted History Tour is heavy on the haunted and the history! This top-rated tour runs every night, mid-April through mid-November, visiting several historical sites including the Old Jail that was built in the 1690s.

There have been many reports of very vivid paranormal experiences happening inside. Sensory equipment is also used to help detect ghost activity. If you’re interested in a hair-raising historical tour perfect for spooky season, this is the haunted Cape Cod tour for you!

Cape Cod has some of the coolest beach towns in Massachusetts and awesome places to stay, too.

The next time you’re looking for a fun fall getaway in Massachusetts, consider Cape Cod for your autumn vacation destination!

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