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Cape Cod Fall Bucket List

Fall is finally here and we've put together a Fall Bucket List of some of our favorite things to do in the Fall on the Cape and Islands! Let us know which ones you check off your list. Also, make sure to check out the sponsor, Massachusetts Cranberries for bog tours this Fall.

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 sleeps up to six people and offers amenities perfect for Fall stays, like an outdoor fire pit, BBQ grill, custom cornhole boards, water access for kayaking/paddleboarding, and more! Located centrally to many of the mentioned Fall activities below!

  • Cape Cod Winery Fall Fest - stop by Saturday, October 14th from 12:00 PM to 7:00 PM 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 @capecodwinery

  • Bad Martha Beer Oktoberfest - Oktoberfest is on at Bad Martha Beer in Falmouth! From September 23rd to October 1st, enjoy live music, yard games, beer, food, and more! 

Bad Martha Beer Oktoberfest

Photo by @badmarthafalmouth

  • Pelham House Oktoberfest - Pelham House is ready for Fall! Join them for their 3rd Annual Pelham House Oktoberfest on Sunday, October 22nd from 12 - 6 PM! Enjoy live music all day long, delicious German menu items including house-made jumbo pretzels and apple cider donuts, fun Fall activities for all ages, and of course, all the beer! They are also offering Thanksgiving Dinner again this year. Enjoy Thanksgiving dinner in the comfort of your own home through their Thanksgiving To-Go event or be their guest and enjoy a delicious selection of Thanksgiving favorites with a menu created by their Executive Chef, Daniel Coté, and culinary team. Limited availability, book here!

Pelham House Resort

Photo by @pelhamhospitality

  • 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. Visit the Pumpkin Festival on Saturday, October 14 from 10:30 - 2:30 and enjoy games, food, music, and fun! Stop by during the weekdays from 8:30 AM - 6:00 PM daily!

Morning Glory Farm

Photo by @jkdow

  • Chatham Bars Inn Farm & Farm Frolic - 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.

Photo by @chathamlivingmag

  • 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, Falmouth, or Massachusetts Cranberries 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!

Kandy Korner

Photo by @thekandycorner

  • Yarmouth Seaside Festival - happening October 7th - 9th 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

  • 23rd Annual Wellfleet Oysterfest - gather at Baker's Field on October 14th and 15th to celebrate the Wellfleet Oyster (and clam) fest. Festival hours are 10 AM - 5 PM. Catch the preliminary shuck-off rounds on Saturday, and the final round on Sunday! You must have a ticket to attend. 

Wellfleet Oysterfest

Via @chelseabpeck

  • Cape Cod Brew Fest - join the celebration of American craft brewers and sample from 50+ breweries and over 150 styles of beer on Saturday, September 23rd at the Cape Cod Fairgrounds. The eleventh 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 on Saturday, October 7th from 10:00 AM to 5:00 PM on Main Street and Cross Street. Stop by for family fun, special sales, music, artisans' market, pumpkin decorating, face painting, Cape Abilities Farmers Market, a 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

  • Chatham Pumpkin People in the Park - head to Kate Gould Park on Main Street in Chatham to see these creative pumpkin displays in person October 14th - 31st! 

Photos by @chathamlivingmag

  • Pumpkin Day at Bourne Farm - stop by Bourne Farm on Saturday, October 7th, 9:00 AM - 3:00 PM, rain or shine for pumpkin picking, Fall activities, local crafters, food, hayrides, music, and more! 

Photo by @seascoops

  • Falmouth in the Fall - if you loved running the iconic Falmouth Road Race, Falmouth In The Fall is for you! Run the same race route from Woods Hole and cross the finish line at Shipwrecked! Registration opens September 20th, and race day is Sunday, November 5th. 

Falmouth In The Fall

Photo by @southshorekelly

  • Auto Camp Oyster Fest - the 2nd annual Cape Cod Oyster Fest is sure to be a highlight this Fall! Join Cape Cod Auto Camp on Saturday, September 23rd for a weekend of fresh, local oysters, live tunes, and more!

Cape Cod Auto Camp Oyster Fest

Photo by @autocampcapecod

  • Donut Guide - it's not Fall without an apple cider donut! Stop by one of our favorite donut shops like Captain Baker Donuts, Cape Cod Donuts, The Downyflake, or Michael's Donuts at the Falmouth Farmers Market! Check out our "Best Donuts" guide here!

Captain Baker Donuts

Photo by @captainbakerdonuts

  • 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

  • Sponsor:

Massachusetts Cranberries host bog tours during the Fall harvest. They invite you to learn how cranberries are grown, farmed, and corralled. See where cranberry juice, dried berries, and that delicious Thanksgiving cranberry sauce start. Get up close to a harvest as the Massachusetts cranberry guides take you on a tour showcasing the cranberry bogs of the south shore. Tickets are now open and available here. See you at the bog!

Massachusetts Cranberries

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