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. 

Thank you to our 2025 sponsor, Cape Cod Select Cranberries! Make sure you check them out for all of your cranberry needs this Fall. Known as the premium fresh frozen cranberry grower in MA, their products make the perfect ingredient for all your fall treats. Recipes, cranberries, pantry favorites, and gift ideas can be found on their website here! 

@capecodselect

• Cape Cod Winery Fall Fest - stop by Saturday, October 18th 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 Collection in person! 

Photo by @capecodwinery

• Pelham House Oktoberfest - Pelham House is ready for Fall! Join them for their 5th Annual Pelham House Oktoberfest on Sunday, October 26th from 12 - 4 PM filled with German delicacies including house-made jumbo pretzels and apple cider donuts, lawn games, fall activities, and live entertainment all day long! 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!

Photo by @pelhamhospitality

• Bad Martha Beer Oktoberfest - Oktoberfest is on at Bad Martha Beer in Falmouth! From September 25th - October 15th from 2:00 PM - 6:00 PM, enjoy live music, yard games, beer, food, and more! 

Photo by @badmarthafalmouth

• 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 18th from 10:00 AM - 2:00 PM and enjoy games, food, music, and fun! Stop by during the weekdays from 8:30 AM - 6:00 PM daily!

Photo by @jkdow

• Chatham Bars Inn Farm & Fall Frolic - each season, the farm produces well over 100,000 pounds and 125 varieties of vegetables. On Sunday, October 12th from 11:00 AM to 5:00 PM, embrace the crisp fall season with apple cider, pumpkin picking, live music, seasonal food, produce, and fun activities for the whole family! 

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! 

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! 

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!

Photo by @thekandycorner

• Yarmouth Seaside Festival - happening October 11th - 12th from 10:00 AM - 5:00 PM 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!

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! 

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.

Photo by @georgiemorleyphotography

• 25th Annual Wellfleet Oysterfest - gather at Baker's Field on October 18th and 19th 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. 

Via @frompantomouth

• Shuck! A Day of Oysters and Beer - this year marks the 8th annual Cape Cod Beer Oyster Fest! Join the fun on Saturday, October 4th from 12:00 PM - 5:00 PM for a day full of Oysters from all over the Cape, live music all day, craft beer, local wines, and ciders, cocktails, and a variety of non-alcoholic options. If you are not an oyster fan, there will be other local vendors serving up delicious food. A ticket is required. 

Photo by @capecodbeer

• 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 9th - 31st! 

Photo by @visitcapecod

• Chatham Oktoberfest - check out Chatham's Oktoberfest celebration happening on Saturday, October 18th from 11:00 AM - 4:30 PM at Kate Gould Park. Enjoy live music, family activities such as games and crafts, local vendors and breweries, delicious food, and more!

Photo by @takecarecapecod

• Toney Andrews Farm - located in East Falmouth, enjoy hay rides, pumpkin picking, cornstalks, winter vegetables, and you can even shop their variety of fall decorations while your visiting! Additionally, make sure to stop by every Sunday in October from 11:00 AM - 3:00 PM to check out Sea Scoops ice cream truck. They will be serving their delicious Cider Donut Sundaes that you won't want to miss!  

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 Wednesday September 17th at 9:00 AM, and race day is Sunday, November 2nd at 11:00 AM. 

Photo by @southshorekelly

• Cape Cod Canal Day - a family-friendly event that takes place at Buzzards Bay Park on September 20th from 11:00 AM - 6:00 PM! Enjoy local food trucks, live entertainment, craft beer & wine, children's activities, arts and crafts vendors, and you can even partake in their 5k road race happening at 9:15 AM. 

Photo by @capecodcanalregioncoc

• 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!

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! 

Photo by @bartlettsfarm

• Love Local Fest - join the fun happening on Sunday, September 28th from 11:00 AM to 5:00 PM at Aselton Park in Hyannis! Free and open to the public, enjoy what makes Cape Cod so special - from local makers + brands, to live music, and delicious local food!
  

Photo by @lovelivelocal

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 above!

Check out our Top 10 Places to Stay in the Fall on Cape Cod guide which includes some of the dreamiest cottages - perfect for cozy stays while enjoying all your favorite fall activities.

@seatucketcottage