Warm, sunny days…cool nights…crowds gone…fall is a delightful time to vacation on
the Cape. And, with a large inventory of Cape Cod vacation rentals to choose from, values abound. Whether you come for a week or just
a long-weekend, you’ll find towns all across Cape Cod and the Islands hosting annual
festivals, fairs, and farmer's markets.
Eastham's Windmill Weekend held September 5- 7
is an annual community festival, a fair, and a family party all rolled into one and is held on the weekend following Labor Day. Windmill Weekend is a series of events held on Windmill Green and other locations around town. Activities include a sand art competition, road races, band concerts, arts and craft show, tricycle race, and dancing. Continuous entertainment is held on the Green both Saturday and Sunday. A highlight of the weekend is the public recognition, as Windmill Honorees, of one or more Eastham citizens, who have demonstrated unusual dedication to the town through volunteer activities. Excitement peaks with Sunday’s Parade.
If you are looking for great food don’t miss the Cape Cod Food Truck Festival in Falmouth on September 6. The festival will feature food truck favorites, live music, beer and wine, sampling tents and more! It will feature over 20 of New England’s most popular food trucks serving up a variety of fan favorites, including fresh seafood, Asian fusion, BBQ, local ice cream, gourmet pizza, whoopee pies, and more. The festival will also feature more than two dozen local Etsy artisans. Participating trucks include: Cape Cod Canolli, The Local Scoop, Frozen Hoagies, Cupcake City, Pasta Pot, Munchies Food Truck, Uyghur Kitchen, M&M BBQ Ribs, Away Café, and Plouf Plouf Gastronomie.
The 27th Annual Cape Cod Glass Show & Sale will be held on September 6-7. Located at
the Corpus Christi Church in Sandwich, the Show features antique and collectible
American and European glassware from the 18th to 21st century and is open from 10
The Annual Harwich Arts & Music Cranberry Festival will be the weekend of September
13 and 14. The Cranberry Festival will be held at the Brooks Park on Oak Street
in Harwich and will include food, live music, a craft show, a family fun beach day,
and a parade.
Truro Treasures Weekend is September 19-21. The weekend begins on Friday with an historical talk in the afternoon and an evening cocktail party, followed by Saturday and Sunday activities including a pancake breakfast, Historical Society program, arts & crafts show, flea market, kids events, antique appraisals, dog show, silent art auction and live art demonstrations, Saturday evening dinner, 5k run/walk, golf tournament, Highland Center tour, Truro Police Department Tour and K-9 demonstration, antique and classic car show, adult treasure hunt, our closing event, the grape stomp and jazz festival, and much more! The Mission of Truro Treasures is to sponsor a weekend of fun for the entire town of Truro that builds community spirit. Many events are free and when funds are raised they are given back to various local non-profit organizations.
Another great event that weekend is the Celebrate Our Waters Weekend held in Orleans September 20-21.The purpose of the weekend is to showcase the area's precious bays, ponds, lakes, marshes, creeks and beaches and thereby increase general awareness and appreciation of our valuable water resources. The event was originally conceived of as simply a few guided walks highlighting Orleans' ponds and saltwater estuaries but it quickly mushroomed into a two day festival including walks, bike rides, talks, tours, kayak trips, cat boat sailing, aquaculture events, a sand sculpture contest and a bonfire on Nauset Beach.
Rides and games by Rockwell Amusements at the Bourne Scallop Festival
Painted Light Photography
One delicious event is the annual
Scallop Festival held in Bourne from September 29-21. Dubbed the “Largest Scallop
Festival on the East Coast,” the weekend is filled with music, entertainment, a
professional arts and crafts show, rides, games and, of course, scallops. More than
3 tons of scallops will be served to over 50,000 visitors!
If you’re really ambitious and willing to support a great cause, consider participating
in the "Harbor
to the Bay Bike Ride" a one-day bike ride from Boston to Provincetown on
September 20 that improves community awareness and care for people living with HIV and
Enjoy the taste of an IPA, Belgian wheat, or a dark stout? Then make it a point to attend the Cape Cod Brew Fest in Falmouth on September 27. This celebration of American craft brewers and sample from 50+ breweries and over 200 styles of beer. The event will have two, three-hour sessions from 1:00 - 4:00 p.m and 5:30 - 8:30 p.m. Each session will feature live music and food from over a dozen vendors. Food trucks will be on-site providing additional dining options. VIP ticket holders will be able to sample additional rare and specialty beers from select breweries as well as enjoy complimentary food. The Cape Cod Brew Fest is a 21+ event. No one under the legal age will be admitted.
In October, towns all across the Cape and Islands will be showcasing local art and culture with
concerts, special exhibits at art galleries, museums, and theaters, art activities
for children, and more at the 7th annual
Fall for the Arts Festival which runs from October 4 to November 1. Admission
is free, and specials and discounts of all kinds will be offered to visitors at
this terrific, regional event.
A fun event is Barktoberfest in Plymouth on October 4. There are activities for the whole family all day long, Pet-related vendors, food, live entertainment, contests, rabies clinic, blessings and more. Contests for costume, loudest bark, fastest tail wag. Sponsored by the Plymouth Chamber of Commerce.
The weekend, October 11-13, offers the popular Yarmouth Seaside Festival
- a craft fair with more than 125 crafters, a parade, live entertainment, kayak
and canoe races, a 5K road race, a pie-eating contest, fireworks, and more.
Photo courtesy of Lezli Rowell for SPAT
Annual Wellfleet Oysterfest
One of the most popular events is the annual
Wellfleet OysterFest which runs from October 18-19. This two-day street party
celebrates the town's famous oysters, clams and shellfishing traditions and brings
together locals and visitors alike for a weekend full of hometown flavor and big
time fun. Entry is free, and highlights include local cuisine, arts and crafts,
children's activities, educational exhibits, live music and the Oyster Shuck-Off
competition. There are a number of satellite events planned: beachcombing and bird
walks, a 5K road race and children's fun run, cooking demonstrations, tasting seminars,
book talks, and oyster grant tours.
Are you a runner? Then you won't want to miss the Cape Cod Marathon Running Weekend in Falmouth the weekend of October 25-26. From its inception in 1978, the race has been a Falmouth Track Club event. In 1993 a marathon relay was added to the event and has grown to 210 teams. 2011 was our first year for the half marathon, it has proven to be a popular event that fills early each year, and it will continue to be held on Saturday morning creating a true Cape Cod Marathon Running Weekend!
Fall Events on Cape Cod.
Fall highlights on Martha's Vineyard and Nantucket.