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. 

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 19th 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! 

Photo by @capecodwinery

• Pelham House Oktoberfest - Pelham House is ready for Fall! Join them for their 4th Annual Pelham House Oktoberfest on Sunday, October 27th from 12 - 6 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 October 1st - 13th, 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 19th from 11:00 - 2:00 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 & Farm Frolic - each season, the farm produces well over 100,000 pounds and 125 varieties of vegetables. Embrace the crisp fall twilight with Chatham Bars Inn Farm Dinner season with a magical Greenhouse Dinner Series. This fall series will be at their picturesque 8-acre farm every Friday from September 20th to November 15th. Come enjoy a delicious farm-to-table meal with vegetables and flowers lining the tables!

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 12th - 14th 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

• 24th Annual Wellfleet Oysterfest - gather at Baker's Field on October 19th and 20th 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 @chelseabpeck

• Shuck! A Day of Oysters and Beer - this year marks the 7th annual Cape Cod Beer Oyster Fest! Join the fun on Saturday, October 5th 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 12th - 31st! 

Photos by @chathamlivingmag

• Pumpkin Day at Bourne Farm - stop by Bourne Farm on Saturday, October 12th, 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 28th, and race day is Sunday, November 3rd. 

Photo by @southshorekelly

• Auto Camp Oyster Fest - the 3rd annual Cape Cod Oyster Fest is sure to be a highlight this Fall! Join Cape Cod Auto Camp for a weekend of fresh, local oysters, live tunes, and more. Stay tuned for the 2024 date coming soon!

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!

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