When the air turns crisp and the leaves take on brilliant hues, Talbot County becomes the perfect fall getaway. From cultural experiences and waterfront heritage to farmers markets and seasonal festivals, there’s no better time to explore Maryland’s Eastern Shore. Here are five reasons you’ll want to plan your autumn escape.
1. Soak in Live Performances That Warm the Soul
Cooler nights set the stage for unforgettable entertainment. The historic Avalon Theatre in Easton draws nationally recognized musicians, comedians, and performers, while the intimate Ebenezer Theater offers a stunning space for classical and contemporary concerts, including the Chesapeake Music Interlude Concert Series. Together, these venues make Talbot County a top destination for live arts.
2. Savor Fresh Flavors of the Season
Fall means harvest, and local watermen and farmers are hard at work, readying their freshest bounty of the season.
There’s no better place to savor the succulent and salty flavors of the Chesapeake Bay than in Talbot County, where the oyster is celebrated during colder weather months. These briny bites are a seasonal must and served at a variety of different ways at many local restaurants.
On Saturday mornings, farmers markets overflow with autumn’s best. The Easton Farmers Market, one of the oldest in the nation, offers a rich tapestry of local flavors and community spirit. You can often shop to the sounds of live music, provided by the Avalon Foundation. Held in the municipal parking lot on Harrison Street, this market continues past summer and is open year-round.
The St. Michaels Farmers Market runs Saturday mornings, 8:30-11:30 a.m. through November at 206 S. Talbot Street. This market has been going strong for over 25 years and emphasizes the importance of eating #postivelylocal. In addition to farmers and food growers, you can also find live music, pop-up vendors, and educational exhibits from local community groups.
3. Explore History and Heritage by Land and Water
Talbot County turns 365 in 2026. Explore this rich history through Talbot County’s network of museums, the centerpiece of which is the 18-acre Chesapeake Bay Maritime Museum. Exhibits tell the story of the Chesapeake Bay’s people and places. If you’d prefer to explore on your own, follow the Frederick Douglass Driving Tour. The famed abolitionist was born into slavery in Talbot County, and this four-part tour explores the county through his eyes.
4. Celebrate Seasonal and Spooky Fun
Pumpkins, hayrides, fall spices, and spooky stories abound in Talbot County. When its pumpkin picking time, families have enjoyed Councell Farms for over 40 years. The ‘Field of Fun’ at this family-run farm offers a corn maze, combine slide, and pumpkin patch. Head to A Family Affair Farm for Flashlight Nights on weekend nights to navigate their 3-acre maze after dark – don’t forget your flashlight!
If you’ve embraced the taste of pumpkin spice and other seasonal flavors, you can warm up with a cup from the original Rise Up Coffee location or another of Talbot County’s roasteries. For those surprisingly warm fall days, cool down with a scoop from a Talbot County creamery, where ice cream is churned into art.
For those who enjoy a thrill, Chesapeake Ghost Tours offers lantern-lit walks through Easton and St. Michaels. With tales of haunted inns, restless spirits, and centuries-old legends, these tours blend history with a touch of mystery—perfect for the season.
5. Get Festive as Talbot County Celebrates Fall
Autumn in Talbot County is marked by beloved festivals that draw visitors from near and far. The events and festivals below can be found on our calendar, along with many other activities.
In October, Easton’s Fall Kick-Off commemorates the start of the season, with a giant pumpkin trail and on-site carving along the brick-lined streets of Downtown Easton. Whether you’re a cinematic extraordinaire or just looking for a fun weekend getaway, the Chesapeake Film Festival promises an unforgettable experience. Embrace the spirit of a Chesapeake Bay waterman during the annual Tilghman Island Day, which not only highlights local seafood, but offers boat docking, workboat races, and crab picking contests. The celebration of the Chesapeake Bay’s seafood bounty continues at Oysterfest, where the Bay’s favorite bivalve takes the spotlight. Enjoy a traditional community celebration during Oxford’s Fall Fest, which includes an Oktoberfest menu and scarecrow contest.
The season culminates with the Waterfowl Festival. Commemorated like a holiday by locals, the long-running event spans three days, drawing attendees from throughout the Mid-Atlantic. The festival celebrates Eastern Shore heritage, encapsulating the history of waterfowl traditions dating back centuries and recognizes artists who strive to represent these traditions in their work.
Plan Your Fall Escape in Talbot County
With vibrant arts, seasonal flavors, rich heritage, and festivals that capture the spirit of the Chesapeake Bay, Talbot County shines bright in the fall. Plan your visit, cozy up in one of our welcoming lodging options, and discover why autumn is the perfect season to experience Maryland’s Eastern Shore.
