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 Assateague Island with its wild horses. 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 the beauty of Assateague Island and its wild horses, visit the historic town of Berlin, and immerse yourself in the culture of St. Michaels and Tilghman Island.

  • Signature Farm Dinner: Enjoy a gourmet farm-to-table dinner curated by Modern Stone Age Kitchen that highlights 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)

Join us for three days of cycling, exploring, and indulging in the best of Maryland’s Eastern Seashore on and off the beaten path.

  • Meeting Time: 9am

    Meeting Location:
    Wilmer Park (On the Water)
    Chestertown, MD

    9am Welcome: Enjoy local pastries and coffee as we meet our guides and fellow riders to discuss the day and the weekend’s itinerary.

    Scenic Cycling: Choose your ride: Both short, casual ride or a long, fast-paced rides are offered! Enjoy snacks and hydration at farm stops along the way. Check out the sample routes below!

    Experiences: Today we will explore Maryland’s Eastern Shore coastline and learn about its farmers that get their hands wet as well as dirty!

    Dinner: Gourmet locally-sourced dinner by Modern Stoneage Kitchen, a family-run unique culinary destination where everyday foods are artfully transformed into the healthiest versions using ancestral and traditional cooking methods.Scenic Cycling: Warm-up ride. Enjoy snacks and hydration at farm stops along the way. Check out the sample routes below!

  • Meeting Time: 9am

    Meeting Location:
    Wilmer Park
    Chestertown, MD

    9am Welcome: Enjoy local pastries and coffee as we discuss our ride and experiences.

    Scenic Cycling: Choose your ride: Both short, casual ride or a long, fast-paced rides are offered! Enjoy snacks and hydration at farm stops along the way. Check out the sample routes below!

    Experiences: Today we will explore Maryland’s Eastern Shore coastline and learn about its farmers that get their hands wet as well as dirty! We will have optional and recommended local activities after the ride.

    Dinner: On your own

  • Meeting Time: 9am

    Meeting Location:
    Bayside Landing Park
    Rockhall, MD

    9am Welcome: Enjoy local pastries and coffee as we discuss our ride and experiences.

    Scenic Cycling: Casual ride to visit a protected island.

    Experiences: Today we will learn the unique species of bald eagles and other birds

    End on a High Note Lunch: Celebrate our great weekend with a farewell lunch after our invigorating ride. It's the perfect time to recap our weekend and share photos with a toast to an incredible adventure. We end our tour around 2-3pm

  • 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

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!