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Fall 2019 on Cape Cod

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 6 - 8 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’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 14 that improves community awareness and care for people living with HIV and AIDS.

The 32nd Annual Cape Cod Glass Show & Sale will be held on September 14 - 15. Located at the Cape Cod Community College in Barnstable, the Show features antique and collectible American and European glassware from the 18th to 21st century and is open from 10 to 5 on Saturday and 11 to 4 on Sunday.

The Annual Harwich Arts & Music Cranberry Festival will be the weekend of September 14th and 15th. 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 20 - 22. 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 20th. 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.

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 21st. This celebration of American craft brewers and sample from 60+ breweries and over 200 styles of beer. The event will have one session from 2:00 - 5:30 p.m. The festival will feature live music and food trucks & vendors will be on-site for purchase. Every attendee will receive a custom glass. A portion of every ticket sold will benefit the Barnstable County Agricultural Society. The Cape Cod Brew Fest is a 21+ event. No one under the legal age will be admitted.

The weekend of October 12th - 14th 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.

Oyster Shucking
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 19 - 20th. 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 26th - 27th. 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!

Find more Fall Events on Cape Cod.

Fall highlights on Martha's Vineyard and Nantucket.

About Joan Talmadge

About Joan Talmadge: My husband Jeff and I created in 1997, shortly after buying our Cape home. My background includes teaching fifth grade for 8 years and writing and editing educational publications for 15. I get great joy from helping fellow homeowners successfully rent their homes. Jeff and I are proud to have two of our three grown children working for, truly a family-run business. For me, the Cape and Islands are magical all times of the year -- whether it's walking on Nauset Beach, playing golf, or enjoying family and friends.