Lower Cape “Second Summer” Guide: Fall Festivals & Events You Can’t Miss

Living on Cape Cod Heather MacDonald September 16, 2025

A Guide to Fall Activities on the Lower Cape: “Second Summer” Edition

As summer winds down, the Lower Cape doesn’t slow—it shifts into a warm, golden-pace rhythm. Between Provincetown, Truro, Wellfleet, Eastham, Orleans, Chatham, Harwich, and Brewster, there are vibrant festivals, family fun, and seasonal traditions that make fall on Cape Cod something special. Here’s your curated guide to what’s happening this year—and what you won’t want to miss.

Highlight Annual Events & Traditions

Here are the recurring fall events—festivals, displays, performances—that define “Second Summer.”

Event	When & Where	What Makes It Special
Eastham Windmill Weekend	September 5-7 in Eastham Cape Cod Chamber	Celebrates small-town charm with a parade, live music, crafts & family fun on the village green. Great for exploring local culture. Cape Cod Chamber
Harwich Cranberry Arts & Music Festival	September 13 & 14 in Harwich Cape Cod Chamber	Over 100 artisan vendors and food trucks, live music, and a real community festival feel. A wonderful way to sample local arts, foods, and fall flavors. Cape Cod Chamber
Cape Cod Canal Day	September 20 (location near the Cape Cod Canal) Cape Cod Chamber	Family-friendly activities: food trucks, live music, kids’ events and more. A relaxing way to enjoy the outdoors and local vendors. Cape Cod Chamber
Tennessee Williams Theater Festival	Late September (around Sept 25-28) in Provincetown Cape Cod Chamber	A cultural highlight—plays, readings, discussions rooted in Provincetown’s artistic heritage. Perfect for arts lovers. Cape Cod Chamber
Mashpee Oktoberfest	Early October in Mashpee Commons Cape Cod Chamber	German biergarten style fun, pumpkin decorating, craft booths, family-friendly activities, live music. Great way to usher in fall. Cape Cod Chamber
Vinegrass Music Festival	Early October at Truro Vineyards Cape Cod Chamber	Americana / bluegrass / folk music, wine/spirits, food trucks, beautiful vineyard setting in the Outer Cape. Relaxed, festive. Cape Cod Chamber
Wellfleet OysterFest	Mid-October, Wellfleet Cape Cod Chamber	Celebrates Wellfleet oysters with raw bars, shuck-offs, live music, lectures, kids’ crafts. A beloved local tradition. Cape Cod Chamber
Chatham’s Pumpkin People in the Park	October 14-31 in Chatham Cape Cod Chamber	Kate Gould Park transforms with creative pumpkin “people” displays by locals/businesses; also aligned with Chatham’s Oktoberfest. Great photo ops & fall charm. Cape Cod Chamber
Chatham Oktoberfest	October 18 in Chatham Cape Cod Chamber	Family celebration, fall food, live music, festivities in Chatham’s Main Street / Kate Gould Park area. Cape Cod Chamber

Things to Do Beyond the Big Events

Alongside these standout festivals and traditions, enjoy these perennial fall favorites across the Lower Cape towns:

Beach walks & sunset views — With fewer crowds, the beaches in Provincetown, Wellfleet, Eastham, and Orleans are perfect for long, peaceful strolls, low-tide explorations, and vibrant sunsets.
Trail hikes & National Seashore paths — Trails like Fort Hill in Eastham, the Province Lands in Provincetown, and the many paths through Wellfleet’s marshes offer fall foliage and tranquil scenery.
Biking the Cape Cod Rail Trail — Cooler air and diminishing traffic make this an especially good time to ride. Orleans, Eastham & Brewster sections are scenic and accessible.
Farm stands & markets — Look for fall harvest items: apples, pumpkins, cider. Also local crafts; many artisans tie into the festival circuit.
Cultural arts & galleries — Provincetown, Truro, Wellfleet, and Chatham have arts scenes that stay active into the fall. Galleries, theater performances, music, and artist talks.