Autumn is a magical time on Maryland’s Eastern Shore, especially in Talbot County, where charming towns like Easton and St. Michaels come alive with fall colors, waterfront breezes, seasonal food, and community spirit. Whether you're a foodie, a family, or a couple looking for a cozy weekend getaway, there’s something happening this fall just for you.

Here’s a curated guide to the best upcoming events from late September through October 2025, plus ongoing seasonal fun you won’t want to miss.

📅 Fall 2025 Events in Easton & St. Michaels

🍷 September 24, 2025 — Sip & Paint at Kim Hovell Studio

Where: St. Michaels

Enjoy a relaxing evening of creativity and wine at this boutique art studio. Led by local artists, these guided painting sessions are fun, no-pressure, and perfect for a date night or girls' night out.

🎃 October 3–4, 2025 — Easton Fall Kickoff Weekend

Where: Downtown Easton

Celebrate the start of fall with a weekend full of activities: pumpkin trails, live music, pumpkin painting for kids, outdoor movies, art shows, and exclusive food and drink specials from local restaurants. Easton truly comes alive with color and creativity this weekend.

🍽️ October 11, 2025 — Fall Taste of St. Michaels

Where: Downtown St. Michaels

Take your tastebuds on a tour of town! Local restaurants, bakeries, and eateries offer tastings, small bites, and fall-themed treats all day long. Stroll the scenic streets while sampling the very best of Eastern Shore cuisine.

👒 October 18, 2025 — Fall Into St. Michaels Festival

Where: St. Michaels

This family-friendly harvest celebration includes a scarecrow-decorating contest, pumpkin painting, sidewalk sales, pie-baking contests, and even a dog costume parade (Wag-O-Ween). A wholesome, festive day that welcomes locals and visitors alike.

🦪 October 25, 2025 — St. Michaels Oyster Festival

Where: St. Michaels

Celebrate Maryland’s beloved bivalve at this oyster-centric festival! Enjoy raw oysters, fried oysters, oyster stew, local beer, live music, and artisan vendors. Fall is oyster season on the Eastern Shore — this event is the real deal for seafood lovers.

🧺 Weekly & Seasonal Favorites

Even when big events aren’t happening, there’s still plenty to enjoy each week this fall:

• St. Michaels Farmers Market – Every Saturday morning (8:30–11:30 AM) through November. Fresh produce, local flowers, baked goods, and more in the heart of town.

• Easton Farmers Market – Saturday mornings through mid-December. A community hub for everything local, seasonal, and delicious.

• Classic Motor Museum of St. Michaels – Open weekends. Explore vintage vehicles and learn about Eastern Shore transportation history. Great for families or history buffs.

🌅 Why Visit the Eastern Shore in Fall?

• Scenic Beauty: With its waterfronts, historic homes, and colorful foliage, Talbot County offers some of the most Instagram-worthy views in Maryland.

• Cozy & Walkable Towns: St. Michaels and Easton both offer an intimate, small-town vibe with top-tier dining, shops, and inns.

• Less Crowded, More Relaxed: Unlike the summer rush, fall is a quieter time to visit, with easier parking, shorter lines, and a more laid-back experience.

• Fall Food Culture: Oysters, crab soup, cider, pumpkin treats, and more—local restaurants embrace the season deliciously.

✨ Plan Your Visit

• Where to Stay: Check out boutique inns in St. Michaels or charming B&Bs in Easton. Book early for festival weekends.

• What to Pack: Layers! Fall weather on the Shore is unpredictable—cool mornings and warm afternoons.

• Getting Around: Both towns are walkable, but having a bike or car makes it easier to explore the whole county.

🍁 Wrap-Up

Whether you're a longtime Shore lover or a first-time visitor, Fall 2025 is shaping up to be full of flavor, festivity, and fun in Talbot County. Mark your calendar, bring your camera, and don’t forget to grab an oyster or two while you’re here.