May 23-25, 2025

Weekend Getaway

Chestertown, Maryland

A TASTE OF MARYLAND’S eastern shore

Maryland's Eastern Shore offers an adventure filled with the perfect mix of scenic beauty, rich history, and charming town. Designed for cycling enthusiasts, the tour features rides through charming towns along the picturesque Chesapeake Bay, with short and long route options. Along the way, we’ll stop at local farms, enjoy fresh dairy delights, and visit the renowned Tilghman Island. For food lovers, savor the region’s rich flavors as we taste homemade ice cream from a working dairy farm, and enjoy the best crab cakes in town.

riding level

Our courses are designed to accommodate riders of all levels, from beginners to avid enthusiasts. The terrain of coastal Maryland is predominantly fat with occasional gentle rolling hills.

What to Expect

  • Scenic Coastal Rides: Pedal through the charming landscapes of Maryland's Eastern Shore, including serene riverside towns, lush farmlands, and picturesque views of the Chesapeake Bay.

  • Farm-to-Fork Delights: Relish in fresh, local flavors with stops at a dairy farm to enjoy from "cow-to-cone" ice cream, local seafood and produce from the region's vibrant farms, all paired with locally crafted beverages.

  • Unique Experiences: Explore historic Chestertown as it comes alive with the annual Tea Party Festival; immerse yourself in the culture of St. Michaels and enjoy the nature and beauty of Tilghman Island with optional excursions including a full day option bike ride and day trip to Assateague Island National Seashore. Ride among the wild horses and enjoy coastal flavors.

  • Signature Farm Dinner: Enjoy a gourmet farm-to-table dinner by Crow Vineyards and Winery highlighting the best seasonal ingredients from Maryland’s Eastern Shore.

Limited to 30 participants

Food & Drink

Enjoy the freshest steamed blue crabs and crab cakes paired with Maryland’s Riesling or famous Orange Crush cocktail.

unique farm experiences

Savor the bounty of its strawberry fields and orchards, and raise a glass to locally crafted brew at Lockbriar Farms

explore

Discover Maryland's Eastern Shore's rich history, where colonial settlements and maritime traditions blend with the Native American tribes like the Nanticoke and Choptank, who thrived on the region's abundant waterways for fishing, trade, and sustenance.

Weekend Getaway details

Friday, May 23 - Sunday, May 25, 2025

$699 plus fees (lodging and bicycles not included)

Sunday Option to Explore Assateague Island National Seashore. Bike among the wild horses!

Join us for three days of cycling, exploring, and indulging in the best of Maryland’s Eastern Seashore on and off the beaten path. Route daily experience details will be shared to participants once registration is complete.

  • 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);45miles (long ride) mostly flat

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

    Meeting Location:
    Easton, MD. Details provided to participants with registration

    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 throught 4 charming historic towns, 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 including St. Michaels. A ride to Tilghman Island welcomes us with its working watermen’s village, oyster boats, and rich maritime traditions.

    In Oxford, we board a ferry 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 at a local gem. 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

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

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

    Meeting Location:
    Chestertown, MD 21620

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

    9am Welcome: Today’s experience embraces the mission of Farm to Fork with a ride focused on visiting and supporting local farms and surrounding communities. We will begin our journey after a bike brief and introduction.

    Highlights of the day include:

    • Three farm visits, including a hydroponic farm where we’ll not only enjoy farm-fresh local bites but also learn about hydroponic growing techniques.

    • Our tour also features a post-ride lunch offering a classic Maryland experience with a fresh, locally sourced meal.

    • A stop at Rock Hall, a charming waterfront town known as the “Pearl of the Chesapeake.”

    • A ride into Eastern Neck National Wildlife Refuge, a pristine haven for bald eagles, herons, and migratory waterfowl with panoramic Chesapeake Bay views and the untouched beauty of this protected sanctuary.

    • The ride and light lunch will conclude around 2:00 PM, allowing riders the rest of the afternoon to relax or explore the town and festival at their own pace.

    • In the evening, we’ll gather for our Signature Farm Dinner Experience at Crow Vineyard and Winery for a gourmet dinner with wine pairing curated by a local chef for hands on experience.

  • Sunday Option 1: LOCAL RIDE — Chestertown Coastal & Inland Ride

    Meeting Time: 9am
    Meeting Location:
    1860 Brampton Inn B&B
    25227 Chestertown Rd
    Chestertown, MD 21620

    Highlights include:

    • Chestertown Coastal and Inland Ride (Approx. 30 miles) — Enjoy a scenic coastal ride beginning and ending at the historic 1860 Brampton Inn B&B. The ride concludes around 12:00 PM.

    • Tea Time and Light Lunch (included) at the 1860 Brampton Inn.

    • Spend the remainder of the afternoon exploring the Chestertown Tea Festival at your own pace

    • Bonus (included): For guests staying over Sunday night, join us for a 7:00 PM Sunset Sailboat Cruise — the perfect way to cap off a memorable weekend!

    ________________________________________

    Sunday Option 2: FULL DAY — Assateague Island/Ocean City Adventure

    Meeting Time: 7:30am (If traveling with Farm to Fork by Transport Van)

    Meeting Location:
    1860 Brampton Inn B&B
    25227 Chestertown Rd
    Chestertown, MD 21620

    Meeting Time: 10:00am (If arriving independently to Assateague Island Visitor Center)

    Assateague Island Visitor Center
    11800 Marsh View Ln,
    Berlin, MD 21811

    Highlights include:

    • Assateague Island/Ocean City Adventure (30–42 miles) — Venture to Assateague Island for a beautiful ride through protected nature preserves, home to the island’s famous wild horses.

    • Visit two farms on the mainland before heading to Ocean City for a relaxing late lunch and free time to stroll the boardwalk.

  • 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.

  • Includes:
    Redman Farms

    Lockbriar Farms

    Crow Vineyard & Winery

    Chestertown Tea Party

  • Bike Rental: Easton Cycle Sport

    Hotel: Recommend to book in/near Chestertown, MD

    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.

Sample Long Route

Sample Short Route


Meet your tour director

Your weekend adventure will be led by one of Farm to Fork’s owners, Pina Finazzo, along with experienced lead bike guide(s) and a dedicated SAG support team. Together, they’ll ensure a seamless, enjoyable, and unforgettable experience every step of the way.


Reserve Your Spot Today!

Spaces are limited to just 30 participants. Don’t miss your chance to explore Maryland’s Eastern Seashore!