Cape & Islands - Fall Fun!

Labor Day marks the (un)official end of the Summer season. The college students have left their summer jobs and are back to classes. K - 12 students are enjoying school and fall sports. School buses are rolling and so are the tour buses! The sun is rising later and setting earlier, the days are getting shorter, and Cape Cod air turns cooler and drier. There is plenty of parking at the beaches, traffic has eased up on the major roads, and most of the out of state plates are gone. Don't close up the summer cottage or hunker down inside just yet...

Get outside and enjoy all the Cape & Islands has offer outdoors during the glorious fall months!

Several towns celebrate the spirit of community, the change of seasons, or the fall harvest with local festivals that include something for everyone. The 4th annual Outer Cape Music Festival - two days of live music, community, and giving back on the Outer Cape is a ticketed event on September 5th & 6th at Wellfleet Town Pier -go for 1 day or go for both. Outer Cape Music Inc. has donated thousands to local nonprofits including Lower Cape Outreach Council and The Lily House. OCMF continues to grow music scholarship program to help young musicians on Cape Cod! The annual Eastham Windmill Weekend, is "a community festival, a fair, and a family party all rolled into one", held on the weekend following Labor Day. Activities include a sand art competition, road races, band concerts, arts and craft show, tricycle race, dancing, a parade along Route 6, food and more. The 15th Annual Martha's Vineyard Wind Festival is September 5th at Ocean Park, Oak Bluffs. Say goodbye to summer while celebrating wind with kite making, kite flying, Frisbee games, model sailboat racing, kite boarding, musical entertainment and more!

The Harwich Cranberry Arts & Music Festival, celebrating it's 50th year, feaures vendors selling handmade craft items, food trucks, live music, kids events at the Harwich Community Building on Saturday September 19 and Sunday September 20. Don't miss the fireworks on Saurday! Orleans Pond Coalition hosts the annual "Celebrate Our Waters" festivities on Friday, September 18 through Sunday, September 20. A weekend of photography & art, poetry, live music, water sports, tours, kids activities and so much more - see complete schedule as some events require advance registration. Cape Cod Canal Day takes place at Buzzards Bay Park on Saturday Sept 19 and includes something for everyone - a 5K Race, Live music, Art & craft vendors, Food trucks, Craft beer & wine, and children's activities. Sandwich Arts Alliance hosts the tenth annual Sandwich PorchFest 2026 on Saturday September 19th with local artists playing genres from Americana, Folk, Singer/Songwriter, Rock, Classic, Jazz to Traditional Irish music on porches through Sandwich Village. Falmouth Fall Festival at Falmouth Museums on the Green, a day of family fun and educational adventures, Saturday September 28th - explore scenic gardens & historic buildings with friendly guides who bring Falmouth’s rich history to life. Highlights include a husking bee reenactment, pumpkin patch, storytelling, kid’s games, music by the Falmouth Fiddlers, and farmers market.

The fun continues into October, starting with - 12th Annual Vinegrass Music Festival on Sunday October 4^th at Truro Vineyards in North Truro - this is a ticketed event with proceeds to help in Vinegrass' efforts to purchases instruments for Cape Cod kids, and fund college scholarships and grants for camps. The Annual Yarmouth Seaside Festival runs October 10th & 12th - featuring: Fireworks!, giant craft fair, kid's rides, children's tent, Seaside Clowns, musical entertainment, African Dance & Drums, magician, demonstrations, farmers market, 5 K road race, sandcastle contest, lots of food vendors! Parade on Sunday. Visit seaside festival website for complete schedule! The 26th annual Wellfleet OysterFest celebrates Wellfleet’s famous oysters and its deep-rooted shellfishing traditions with a Shucking Contest, Fine Arts & Crafts Fair, 5K Road Race & Tennis, and more. This year's event takes place on Saturday, October 17 and Sunday, October 18 at Baker's Field. Don't miss this street party of food, art, live music, fun and games for children of all ages! Head to Main Street Hyannis on Sunday October 18th for Hyannis Open Streets - a Family Friendly event featuring entertainment including live music (some of our favorite local musicians), Touch a Truck, crafts, free books from the Hyannis Public Library, face-painting, games and more! Provincetown Tennessee Williams Theater Festival has honored Tennesse Williams, celebrating his Cape Cod connections, by presenting his classic and undiscovered plays. This year's festival 2026 is Pop-up Event, October 8^th thru the 11^th in New Orleans.

For those who prefer the solitude of nature, the cooler crisper weather makes for a perfect day of hiking, biking or fishing on Cape Cod and the islands of Martha’s Vineyard & Nantucket. The Cape Cod National Seashore stretching from Eastham to Provincetown has several walking trails and bike paths, in addition to the beaches which are still nice to visit in the fall. The Mass Audubon Wellfleet Bay Wildlife Sanctuary consists of woodlands, salt marsh, barrier beach and heath lands. Its 5 miles of scenic trails wind through the habitats of a wide variety of wildlife, including songbirds and shorebirds. Other Mass Audubon Cape Cod & Island sanctuaries are located in Barnstable, East Falmouth, Wareham, Vineyard Haven, and Nantucket. See our list for more Cape Cod Hiking Trails. Start a family tradition - Crow Farm in Sandwich offers "Pick Your Own Apples" on certain weekends during the fall! Last, but certainly not least, check out our fishing page to book a Cape Cod fishing charter and catch some fish and excitement!

As always, for wonderful places (and off season specials!) to stay on the Cape check out AllCapeCod.com Lodging; for Nantucket see AllNantucket.com, and for Martha's Vineyard visit AllVineyard.com. Come spend Fall on The Cape and Islands!