Maryland > St. Michaels Weekend, Maryland

2019 Dates: May 10-12, Oct. 18-20 (sold out)

Celebrate spring or savor the fall with a weekend of easy coastal riding on quiet roads. Visit a fascinating variety of historic Tidewater villages and indulge in local cuisine including clams, oysters, and the best crab cakes in the world. Our tour is based in the quaint waterfront town of Saint Michaels, whose historic streets are lined with Colonial-era houses and shops, evidence of its former eminence as a prosperous shipping and trading center. While in Saint Michaels, we are guests at the beautiful Harbour Inn where each of our elegant rooms enjoys a beautiful view of the harbor and the Miles River and where you can opt for a relaxing spa treatment or massage to unwind after your day of cycling and sightseeing. While in Saint Michaels, you might take the opportunity to explore the highly regarded Chesapeake Bay Maritime Museum, where you can learn about the history of the bay and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouses, and several historic vessels docked at the waterfront boat yard.

Finally, the biking on this tour is perfectly designed for an early springtime or fall outing. Easy terrain, quiet tree-lined back roads, and beautiful vistas along the bay make for a wonderful weekend experience.

St. Michaels, Maryland Bike Tour Itinerary

FRIDAY | Arrival Day | Harbour Inn

We begin our tour in the quaint waterfront village of Saint Michaels. Saint Michaels is situated on a picturesque peninsula between Tilghman Island and Easton and is well known for its interesting mix of history, shops, and small town charm.

SATURDAY | Distance: 26 or 38 miles | Terrain: Easier |Harbour Inn

Today’s ride features spectacular cycling on what is considered one of the premier biking routes on the East Coast. We ride a bike path through Easton and wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well-known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch, and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After our crossing we ride pretty back roads through Royal Oak and Bellevue arriving back in Saint Michaels in time for a visit to the Chesapeake Bay Maritime Museum.

SUNDAY | Distance: 27 miles (with shorter option)| Terrain: Easier |Harbour Inn

Our Sunday riding takes us north passing elegant manor houses before crossing the Miles River drawbridge. After passing the “Gothic” ruins of the St. John’s Protestant Episcopal Church (built in 1839), we pass through Unionville and by the historic Unionville cemetery where many soldiers from the Black Unionville Regiment are buried. We then ride the rural roads to the grounds of the “Little Red School House”, a still intact original one-room school built in the late 1800s and which now serves as a museum. From here we loop down along Goldsborough Road and Glebe Road and through Royal Oak back to the Harbour Inn.

St. Michaels Weekend, Eastern Shore of Maryland


Make your reservation with confidence. Your tour is completely 100% refundable up to 60 days of the tour date.

reserveMay 10-12, 2019:  $895
Reserve with $200 deposit

reserveOctober 18-20, 2019:  $895 (Sorry! Sold out)
Reserve with $200 deposit

Final payment due 60 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $220*

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.


St. Michaels Harbour Inn is a luxury inn situated on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.

What’s Included

Tour includes 2 nights of lodging (double occupancy); 2 breakfasts and 2 dinners; all taxes and gratuities at the hotels; free use of bicycle; experienced leaders; full van support; and detailed directions. We have additional optional miles for energetic riders on most tour days.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

Virtual Tour of Maryland