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: Start your Chesapeake Bay bike tour just outside the cute town of Easton, Maryland. On the first day, we’ll ride from Easton to Oxford. Along the way, you’ll see centuries-old churches and cemeteries scattered throughout the gently rolling farmland. We’ll end our ride today in historic Oxford at the beautiful Sandaway Suites. You’ll be able to enjoy spectacular views of the Tred Avon River right from the Sandaway’s expansive lawn or private beach.


Day 2: Hop on the Oxford-Bellevue Ferry to St. Michaels and the Chesapeake Maritime Museum. Once on the island, there are many places to explore! St. Michaels is the home to the Chesapeake Maritime Museum, which you will have the option to tour this afternoon. Lunch is on your own today, so you’ll have a chance to visit one of the charming main street cafes in town. Head back to the ferry, and end your day back at the Sandaway Suites. Dinner is on your own in Oxford tonight.


Day 3: Today we’ll travel on flat, low-traffic rural roads in and around the Blackwater Wildlife Refuge. The refuge has been referred to as the “Everglades of the North,” with one of the largest Bald Eagle nesting colonies in the country. We get to cycle through the conservancy and experience its natural beauty like few others have. Mid-way through the ride, we’ll visit the Harriet Tubman Underground Railroad Historical Park. After the ride, we head back to Easton to check into the Tidewater Inn. We’ll have dinner together as a group this evening to celebrate a fun adventure on the Chesapeake Bay!


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

“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
Bike Tour Routes with Elevation gain and loss
Route Overview
E-bikes Allowed

Required Specifications

  • 50 pounds or less weight limit
  • Class I pedal assist only
  • Removable battery
  • 5+ hour battery capacity

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 | 3 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!

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