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Favorite Things to do in the Fall on the Cape and Islands

We always get asked what some of our favorite things to do in the Fall on the Cape and Islands are, so we decided to put together a list of some of our favorites! Did we miss any? Leave a comment below!

Looking for a place to stay in the Fall? Check out our friends over at, Seatucket Cottage in East Falmouth! Their newly renovated 3 bedroom, 1.5 bath sleeps up to six people and offers amenities such as an outdoor firepit, BBQ grill, custom cornhole boards, water access for kayaking/paddleboarding, and more!

  • Cape Cod Winery Fall Fest - stop by Saturday, October 15th to enjoy live music, delicious food, great wine, and lots of fun. PS make sure you stop by their gift shop and shop our mermaid rings in person!

Cape Cod Winery

Photo by @capeology

  • Chatham Bars Inn Farm - each season, the farm produces well over 100,000 pounds and 125 varieties of vegetables. They host several farm-to-table events which are open to the public and also offer a seasonal farm stand. Come enjoy a welcome reception followed by a 4-course dinner complete with vegetables and flowers lining the tables!

Chatham Bars Inn Farm

Photo by @simplymekb

  • 6A Foilage - also known as Old Kings Highway, this scenic drive includes hundreds of historic sites. Along the way, stop by beaches, cranberry bogs, and nature museums!


Photo by @magri_photography

  • Pumpkins at the Congressional Church in Chatham - one of the most photographed Fall photo spots on the Cape! All proceeds from the pumpkins go to charities, such as The Chatham Children's Fund.

Congressional Church

Photo by @kerrycapecod

  • Visit the cranberry bogs - cranberries are one of only three fruits that are native to New England, they're a Cape Cod icon. Visit Harwich, Sandwich, Dennis, or Falmouth to see one in person! 

Cranberry Bogs

Photo by @nick_haveran

  • Crow Farm - founded in 1916, Crow Farm is a 50-acre family farm located just outside historic downtown Sandwich. Stop by for apple cider, apple picking, and their impressive corn maze! 

Crow Farm

Photo by @dennisjweeks

  • Candy Stores - stop in and stock up on fall goodies from some of our favorite local spots: Chatham Candy Manor (Chatham), The Penney Patch (Provincetown), and Kandy Korner (Hyannis) to name a few!

Chatham Candy Manor

Photo by @chathamcandymanor

  • Bartlett's Farm - located steps from Nantucket's south shore beaches, Bartlett's Farm is Nantucket's oldest and largest family-owned farm. They are known for their delicious corn and tomatoes, as well as, their beautiful flowers. Visit their farm kitchen for freshly prepared sandwiches, pastries, soup, and more to take on your Nantucket adventures! 

Bartlett’s Farm

Photo by @bartlettsfarm

  • Morning Glory Farm - started in Edgartown in 1975, Morning Glory Farm grows 65 acres of vegetables and small fruits, as well as, eggs and fresh meat. Stop by during the weekdays from 8:30 AM - 5:30 PM or Saturday and Sunday from 9 AM - 4 PM!

Morning Glory Farm

Photo by @jkdow

  • Yarmouth Seaside Festival - happening October 8th - 10th at Joshua Sears Memorial Field in Yarmouth! Events include an arts & crafts fair, rides & games, live music, kids' entertainment tents, great food, a pie-eating contest, and more!

Yarmouth Seaside Festival

Photo by @lonowrites

  • Visit some local breweries - from Cisco Brewers on Nantucket, to Bad Martha Farmer's Brewery on Martha's Vineyard, all the way to Cape Cod Beer in Hyannis, there are plenty of spots to visit on the Cape and Islands. Check out our "Brewery Guide" here! 

Cisco Brewers

Photo by @ciscobrewers

  • Stroll through all of the different towns - one of our favorites in the Fall to visit is Nantucket. Each town and storefront is decorated so beautifully! Make sure to tag us in any photos you take too.

Downtown Nantucket

Photo by @georgiemorleyphotography

  • Theater Fests in Provincetown - join them for the 16th Provincetown Tennessee Williams Theater Festival happening from Thursday, September 22nd - Sunday, September 25th!

Provincetown Theater

Photo by @paigeashleyrich

  • 22nd Annual Wellfleet Oysterfest - gather at Baker's Field on October 15th and 16th to celebrate the Wellfleet Oyster (and clam) fest. Festival hours are 10 AM - 5 PM. Catch the preliminary shuck-off rounds Saturday, and the final round Sunday! You must have a ticket to attend. 

Wellfleet Oysterfest

Via @chelseabpeck

  • Oktoberfest at Cape Cod Beer - come celebrate beer Saturday, September 17th from 12 - 8 PM at Cape Cod Beer. There will be German-style beers on draft and a German-inspired food menu, along with live music all day!

Oktoberfest Cape Cod Beer

Photo by @capecodbeer

  • Cape Cod Brew Fest - join the celebration of American craft brewers and sample from 50+ breweries and over 150 styles of beer Saturday, September 24th at the Cape Cod Fairgrounds. The tenth annual Cape Cod Brew Fest will be happening from 2 PM - 5:30 PM, with all beverage samples included with the purchase of a ticket, along with a souvenir glass! 

Cape Cod Brew Fest

Photo by @capecodbrewfest

  • Harwich Port Merchants Fall Festival - happening October 8th on Main Street and Cross Street. Stop by for family fun, special sales, music, artisans' market, pumpkin decorating, face painting, Cape Abilities Farmers Market, pie contest, and more! Swing by Buoys On Main located on Main Street in Harwich Port to shop our jewelry line in person!

Photo by @rachdonner

  • Pumpkin People in the Park - head to Kate Gould Park on Main Street in Chatham to see these creative pumpkin displays in person!

Photos by @chathamclothingbar

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