Fall is one of the most magical times to explore Maryland’s Eastern Shore — especially in Talbot County. With crisp bay breezes, tree-lined streets glowing with fall foliage, and warm drinks from cozy coffee shops, Easton and its neighboring towns offer the perfect fall day or weekend getaway.
Whether you're planning a peaceful solo retreat or a couple's weekend, here’s your guide to fall fun, hot drinks, and scenic strolls in Talbot County.
Why Fall Is Perfect in Talbot County
Located just a short drive from the Bay Bridge, Talbot County includes charming towns like Easton, St. Michaels, Oxford, and Tilghman Island — each one full of small-town character, waterfront views, and local flavor.
In the fall, Talbot County comes alive with:
- 🍁 Colorful Foliage along historic streets and country roads
- ☕ Locally Owned Cafés serving pumpkin-spiced everything
- 🎃 Fall Festivals, art walks, and oyster roasts
- 🧺 Farmers Markets filled with apples, gourds, and handmade goods
- 🌅 Bayfront Sunsets perfect for evening walks or wine by the water
How to Spend a Fall Day in Easton & Beyond
☕ Morning: Coffee & Market Hopping
Start your day with a hot drink from a local café (see suggestions below), then stroll through the Easton Farmers Market (Saturday mornings through mid-December) where you’ll find seasonal produce, baked goods, and crafts.
🛶 Midday: Explore the Outdoors
Head to Pickering Creek Audubon Center for a peaceful nature walk among golden marsh grasses and forest trails. Or drive 15 minutes to St. Michaels to walk the harbor and stop by the Chesapeake Bay Maritime Museum.
🌅 Late Afternoon: Sunset & Relaxation
Grab a warm drink and take in a sunset over the Tred Avon River from Oxford’s ferry dock or enjoy a peaceful walk around Idlewild Park.
🍽 Evening: Local Dining & Cozy Comfort
Wrap up the day with dinner at one of Easton’s acclaimed restaurants like Out of the Fire, Bas Rouge, or The Wardroom — many offering seasonal menus with local oysters, root vegetables, and fall desserts.
Top 3 Cozy Coffee Shops in Easton, MD for Fall
1. Weather Gage – Easton, MD
This boutique coffee shop & wine bar on Goldsborough Street has a warm, upscale vibe perfect for fall. They serve great espresso drinks and locally sourced pastries.
📍 101 N Goldsborough St, Easton, MD
2. Rise Up Coffee Roasters – Easton, MD
A local legend with strong coffee, eco-conscious vibes, and great seasonal drinks (try their fall-spiced latte!). The St. Michaels and Easton locations both offer indoor and outdoor seating.
📍 618 Dover Rd, Easton, MD (also in St. Michaels)
3. Bluepoint Coffee – St. Michaels, MD
If you’re venturing into St. Michaels, Bluepoint is a cozy waterfront stop known for its handcrafted coffee and laid-back charm — a perfect mid-morning or late afternoon break.
📍 110 N Talbot St, St. Michaels, MD
Other Fall Fun Around Talbot County
- Easton’s Fall into Easton Festival – A celebration of the season with live music, hayrides, food, and family fun.
- St. Michaels OysterFest (Chesapeake Bay Maritime Museum) – Slurp oysters and enjoy live demos and music in a beautiful waterfront setting.
- Oxford's Fall Art Walks & Open Studios – Discover local artists while walking the tree-lined streets of one of the oldest towns in Maryland.
- Fall Foliage Drives – Explore Tilghman Island and backroads through farmland, waterfront inlets, and historic homes decked out in fall decor.
Tips for Visiting in Fall
- Dress in layers – Mornings and evenings are cool, but mid-days can still feel mild.
- Bring your camera – Foliage and historic buildings make for perfect photo ops.
- Book early – Fall weekends are popular, especially during festivals and events.
- Support local – From coffee shops to artisan markets, you’ll find lots of ways to shop small.
Final Thoughts: Fall in Talbot County Is Pure Magic 🍁
From cozy cafés to waterfront sunsets, Talbot County’s charm is only heightened by the crisp air and golden leaves of fall. Whether you’re exploring Easton’s lively streets, relaxing in Oxford, or strolling St. Michaels’ harbor, your perfect fall day on the Eastern Shore starts with a hot drink and a sense of adventure.
Discover even more seasonal events, hidden gems, and local favorites in my Fall Guide to Maryland’s Eastern Shore — your complete resource for exploring Talbot County this season.