Maryland’s Eastern Shore Bike Tour

Maryland's Eastern Shore Luxury Bike Tour


Chances are, when you think of the Eastern Shore, what comes to mind are crabs, sailing and wedding crashers. There is much more to these sister towns across the Chesapeake than you could possibly imagine. Once you cross over the Bay Bridge, you escape the hustle and bustle of the big cities and suburbs of Baltimore and Washington, DC. In fact, many people have opted for the quieter lifestyle of the Eastern Shore and commute into the cities. Therefore we avoid US Hwy 50.

The charming towns of St. Michaels, Oxford, Easton, Tighman’s Island, Cambridge and Chestertown are loaded with history, National Wildlife Refuges, lighthouses, museums, galleries, wonderful waterfront entertainment, beautiful small inns and upscale establishments and the expanding vineyard industry.

One of the highlights of your tour will be The Harriet Tubman Underground Railroad Park. Another, The Blackwater Wildlife Refuge – with the migratory birds and some of the best marsh scenery outside the Everglades. The Chesapeake Maritime Museum, located in St. Michaels, is loaded with artifacts, exhibits and vessels. The museum dates back to the 1960’s and was once the home to seafood packing houses, working boats and docks. While in the area you will experience the old Oxford/Bellevue Ferry- a 332-year-old, privately-owned ferry, a sunset dinner at Doc’s grill. Don’t miss a stop at the Scottish Creamery, known for their unique flavor of ice cream. Bacon Choclate chip or lavender/honey anyone?

This tour is designed in such a way that you will only change hotels every other night. The Eastern shore is flat, so we classify this tour as being designed for Recreational – Intermediate level rider. Most of our roads are on the quiet back roads that shoot in and out of waterfront communities and towns. We ask riders have some experience riding in light in-town traffic to get to and from our hotels in Easton and Cambridge.


Rider Level

Recreational to Active


25 – 70 miles per day


Travel to BWI airport for an 11am pick up, or meet at the starting hotel in Easton, MD, by noon. We will have a short 2pm tour near town. Drop off time at BWI airport on the final day of riding is 4pm. Do not schedule your flight before 6pm.


All meals are included

Accommmodations (Luxury)

All lodging is included

  • All lodging
  • Transfers to and from the airport
  • All breakfasts, dinners and picnic lunches on riding days
  • Cocktail social hour on the 1st evening of each tour
  • Van support
  • Maps
  • Entrance fees into described museums and parks
  • GPS mapping
  • Mechanic
  • 2 or more experienced guides, familiar with the area
Not Included
  • Airfare
  • Meals on off days
  • Souvenirs
  • 12% gratuity for guides, mechanics, volunteers and tour staff is not included, but greatly appreciated


  • Custom Dates Available
  • 6-Person Minumum


Per Person
  • Single Room Supplement - $540
    Road Bike - $175
    e-Bike: $325
Crabs, seafood and water ... oh my! Book this tour today!


Orientation: Cocktail social hour on the 1st evening

Day 1

Easton loop (22 miles, 367 ft)

Day 2

Easton – St Michael’s – Tilghman Island – Oxford Bellevue Ferry (62 miles, 450 ft)

Day 3

Easton – Hillsboro – Queen Anne – Church Hill (48 miles, 924 ft)

Day 4

Chestertown – Betterton – Rock Hall – Chestertown (56 miles, 1234 ft)

Day 5

Chestertown – Denton – Harmony – Choptank – Cambridge (66 miles, 948 ft)

Day 6

Blackwater Wildlife Refuge and Harriet Tubman Park (56 miles, 257 ft)

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