Why Westport Is Magical in the Fall
Westport, Connecticut, is one of New England’s most charming coastal towns — and fall is arguably the best season to experience it. Crisp mornings, colorful foliage, and a calendar full of community events make it a perfect time to explore. Whether you live here year-round or are visiting Fairfield County, here are some of the best fall activities in and around Westport, CT.
Festivals & Seasonal Events
Westoberfest — October 4, 12–6 PM
Downtown Westport comes alive with over 50 craft breweries, food trucks, and live music. Westoberfest has quickly become one of the most anticipated fall festivals in Fairfield County.
Supper & Soul: Celebrate 60 Years of The Grateful Dead — October 19
The Westport Library is hosting a special tribute concert featuring The Spadtastics, Connecticut’s premier Grateful Dead tribute band. A must for music lovers and a unique fall night out in Westport. View event details here.
Westport Restaurant Week — September 28–October 12
Sample your way through Westport’s vibrant dining scene. Local restaurants will feature prix fixe menus and seasonal specials — the perfect chance to revisit your favorites or discover a new spot.
Harvest & Outdoor Adventures
Westport Farmers’ Market — Thursdays through November 13
Celebrate the fall harvest with farm-fresh produce, artisan baked goods, local cheeses, and seasonal treats. The market is one of the most beloved community traditions in Westport, CT.
Pumpkin & Apple Picking
Nearby farms like Silverman’s Farm in Easton and Jones Family Farm in Shelton are local favorites for hayrides, apple cider, and pumpkin picking — classic autumn fun just minutes from Westport.
Leaf Peeping & Scenic Walks
Westport’s foliage is breathtaking in October. Try a stroll along the Saugatuck River, Winslow Park, or the trails at Earthplace. For a more adventurous hike, head to Devil’s Den Preserve for sweeping fall views.
Sherwood Island State Park
Enjoy a seaside walk along Long Island Sound as the leaves turn. Sherwood Island offers both ocean views and vibrant foliage — a rare combination in Connecticut.
Arts & Culture
MoCA Westport
Cooler days are perfect for exploring contemporary art exhibitions and cultural programming at MoCA Westport.
Westport Museum for History and Culture
Step into Westport’s past while enjoying seasonal tours and fall-themed programs that add a festive twist to local history.
Discover Westport’s Fall Charm
From festive downtown celebrations to serene nature walks, fall in Westport offers something for everyone. These events and activities showcase why Westport, CT, is one of the most desirable places to live in Fairfield County.
Thinking of making Westport your home? The Riverside Realty Group specializes in Westport real estate and luxury homes throughout Fairfield County. Contact us today to find your perfect home in this vibrant community.
