Chesapeake Bay and Maryland Eastern Shore Bike Tour

Bike the Historic Eastern Shore of Maryland

Maryland’s Eastern Shore, Chesapeake Bay, Blackwater National Wildlife Preserve

Imagine pedaling along the coast of the Chesapeake Bay, through the farmlands of the Eastern Shore of Maryland, around historic towns, relaxing on the coast, and dining on fresh oysters and crab cakes, all while enjoying the ease of riding the flat coastal terrain. This is a trip to relish! Due to the coastal weather, this tour is designed to be either your first outing of the year, or your final bike adventure of the season.


Meeting in Easton, Maryland, we will do a quick shuttle to the Cambridge-Dorchester Regional Airport.  Cycling along the bay, through large inland farms and woodlands, and visit the Blackwater National Wildlife Preserve. Blackwater is a haven for several troubled species including the American Bald Eagle, the endangered Delmarva fox squirrel, and the migrant peregrine falcon. The Refuge is unique in that it hosts the largest remaining natural population of Delmarva fox squirrels and is also host to the largest breeding population of bald eagles on the East Coast, north of Florida.  Reflect on your days ride as you lounge in the front yard of the Inn, watching the birds play in the water!

Tour Highlights

Maryland seafood!

Easton Historical District

Blackwater National Wildlife Refuge

Ferry ride to St. Michael's

St. Michael's Maritime Museum

Lodging Options

Sandaway Suites

Tidewater Inn

Day 1: Explore the Chesapeake Bay’s local wildlife at the Blackwater National Wildlife Reserve. Pass by centuries-old churches and cemeteries on your way to Oxford, and the beautiful Sandaway Suites.


Day 2: Hop on the ferry to St. Michaels and the Chesapeake Maritime Museum. End your day back at the Sandaway Suites and dinner on your own in Oxford.


Day 3: Cycle through the Blackwater Wildlife Refuge to see bald eagles, Delmarva fox squirrels, great blue herons and white egrets! Visit the Harriet Tubman historical park, then head back to Easton and enjoy your evening at the Tidewater Inn.


Day 4: Ride straight out of your lodging and through the beautiful backroads of Talbot County. The ride ends where it started, at the Easton Regional Airport.


Custom bike tour departures available for groups of 6 or more.

“My favorite part was visiting Blackwater N.W.P. Having Josh there with his spotting scope and binoculars to help identify the many birds we saw was super.”

~Wiley Grant

Trip Information


Trip Length - Days

New York Finger Lakes Bike Tour
Tour Type
Road Bike
Tour Rating
New York Finger Lakes Bike Tour Elevation
Route Overview

Daily Mileage

Check In Location
Easton Maryland Airport, MD
Maryland Bike tour map
Tour Area
SAG Vehicle New York Finger Lakes Bike Tour
Support & Gear Vehicle

Minimum Age


3 Breakfasts | 4 Lunches
2 Dinners

  • PP Double Occupancy

  • Single Supplement*

  • Standard Bike Rental


*This is required if you are traveling solo or if you are traveling with someone but require separate beds.


Select your departure date and click to reserve your bike tour!