Todays ride through Maryland’s Eastern Shore offers a picturesque blend of coastal beauty, historic charm, and the flavors of the Chesapeake Bay.

Total distance 20-25 miles (short ride);35 miles (long ride) mostly flat

Meeting Time: 9am
End Time: 2pm (ish)

Meeting Location:
Easton MD. (Address TBD)

9am Welcome:
Beginning in Easton, MD, known for its colonial heritage and vibrant arts scene, we embark on a loop through one of the most scenic regions of the Mid-Atlantic. Here we fuel our bodies with local pastries and coffee as we meet our guides and fellow riders to discuss the day and the weekend’s briefing.

Scenic Cycling: We’ll roll out of Easton on quiet, tree-lined roads, passing charming historic homes, local markets, and sprawling farmland. The gentle terrain make for a relaxed warm-up as we head south towards St. Michaels, one of the Eastern Shore’s most iconic waterfront towns. Leaving St. Michaels, the coastline through Eastern Bay Sanctuary, a haven for migratory birds and serene waters, offering a tranquil, nature-immersed ride. Tilghman Island welcomes us with its working watermen’s village, oyster boats, and rich maritime traditions.

From there, we head to Bellevue, where we’ll board the historic Oxford-Bellevue Ferry for a scenic crossing of the Tred Avon River. Arriving ashore, we indulge in a classic Maryland crab feast, savoring fresh seafood, Old Bay seasoning, and local craft spirits with stunning waterfront views. The final stretch back to Easton is a peaceful coast through shaded countryside, where towering oaks complete this unforgettable Eastern Shore day.

Enjoy the rest of the late afternoon on your own.

• Experiences:
  St Michaels: Maritime Heritage and Waterfront

• Eastern Bay Sanctuary: Coastal Beauty & Wildlife

• Tilghman Island Sanctuary

• Bellevue and the Ferry Crossing

Welcome Dinner 7pm: Locally-sourced dinner by Modern Stone Age Kitchen, a family-run unique culinary destination where everyday foods are artfully transformed into the healthiest versions using ancestral and traditional cooking methods.

Today ride is best for: Scenic lovers, history buffs, and seafood enthusiasts

Meeting Time: 9am
End Time: 2pm(ish)

Meeting Location:
Chestertown, MD (TBD)

Distance: 25-30 miles (short) 45-60 miles (long) mostly flat

9am Welcome: After a short briefing we will depart from Chestertown, a charming colonial town on the Chester River.

Scenic Cycling: We pedal through rolling farmland and historic estates. The quiet backroads lead us toward Betterton, where the Chesapeake Bay stretches wide, offering breathtaking waterfront views and a glimpse into this former fishing town’s history.

Todays route also winds inland where expansive fields of corn, soybeans, and wheat define the landscape. Along the way, we will stop at locals best finds including Lockbriar Farms, a family-run gem where farmers dig deep into the soil, harvesting fresh produce, tending to dairy cows, and crafting small-batch ice cream.

Today ride offers an authentic look at Maryland’s agricultural roots, with the scent of earth and fresh crops filling the air.

Experiences:
Lockbriar Farms

Signature Farm Dinner 6:00pm Crow Vineyard & Winery
a working farm and vineyard where a truly special evening awaits. Here, we’ll savor a signature farm dinner, a curated meal highlighting local ingredients, thoughtfully paired with Crow’s handcrafted wines. With the vineyard’s vines stretching into the horizon and the golden glow of sunset, this meal celebrates the rich flavors and hard work of Maryland’s farmers—offering the perfect ending to a ride through the heart of the Chesapeake countryside.

Best for: This ride is perfect for cyclists who love scenic countryside routes, farm-to-table dining & local wines through Maryland’s rich farmland and coastal charm.

Meeting Time: 9am

Meeting Location:
Brampton 1860 Hotel
CHestertone, MD

9am Welcome: After a short briefing, we begin our ride towards Rock Hall Rock Hall, a charming waterfront town known as the “Pearl of the Chesapeake.” Along the way, we pass sweet potato farms, where farmers get their hands dirty harvesting this staple of Maryland’s Eastern Shore.

From Rock Hall, we ride south to Eastern Neck National Wildlife Refuge, a pristine haven for bald eagles, herons, and migratory waterfowl. Cycling through its peaceful marshes and winding trails, we soak in panoramic Chesapeake Bay views and the untouched beauty of this protected sanctuary.

Heading back, we return to Brampton 1860 Hotel just in time for a 1 PM tea service, where we unwind with freshly brewed tea, delicate pastries, and a taste of refined hospitality. If you prefer, skip the tea and head right back into the lively atmosphere of Chestertown’s annual Tea Party Festival, Beer Fest, and Regatta, where history, craft brews, and waterfront excitement bring the town to life—an unforgettable way to end our tour.

Scenic Cycling:

Experiences:
Today, we’ll explore the unique species of bald eagles and other native birds of the Eastern Shore.

We’ll uncover the rich history of sweet potatoes, their significance in local agriculture, and the farmers who cultivate them.

We’ll dive into the fascinating story of the annual Chestertown Tea Party, a festival celebrating revolutionary history with reenactments, regattas, and lively festivities.

End on a High Note Lunch: Today is the perfect time to recap our weekend and share photos with a toast to an incredible adventure. We end our tour around 1-2pm.

Want to join the adventure but only have one day to experience it? We’ve got you covered!

Our single-day option offers the full experience of a day itinerary and includes the Signature Farm-To-Fork Gourmet Dinner. It’s the perfect opportunity to savor the essence of a Farm to Fork adventure and explore the area’s local charm, leaving you the rest of the weekend to explore on your own!

Here’s what you’ll enjoy:

• A fully supported single day cycling tour, farm stops, experiences and meals as listed for Day 2: Saturday, May 24, 2025.

• Signature Farm To Fork Dinner, featuring the finest flavors of the Chesapeake Bay paired with local wine.

• Farm To Fork Goodie bag including a artisan Farm To Fork jersey and more.

Modern Stone Age Kitchen

Redman Farms

Lockbriar Farms

Crow Vineyard & Winery

Chestertown Tea Party

Bike Rental: Easton Cycle Sport

Hotel: Recommend to book in/near Chestertown, MD

• Comfort Inn & Suites start $191.00/nite

• The Brampton 1860 Starts at $369.00/nite

Book Early its a busy weekend in Chestertown

NOTE:

All rides start near Chestertown, MD except Day 1 Friday: Our ride will start in Easton, MD (south of the Chesapeake Bay Bridge). We will end our first day around 2-2:30 pm in time for most hotel check-in.