Bike Tour | Eastern Shore of Maryland / Chesapeake Bay2018-08-16T14:22:21+00:00

Maryland > Bay to Beach

May 6-11 and May 13-18, 2018

Celebrate springtime on the Tidewater Peninsula! Gorgeous, easy biking awaits as we explore the bays and inlets of the Chesapeake Bay and stay in two exceptional properties. Adventure Cyclist magazine calls this one of the ten best places to tour in North America. The roads are mostly at to gently rolling as we wind our way through the Chesapeake estuary and its endless number of small bays and inlets. We offer additional riding for the energetic, so this is a perfect tour to revive your cycling legs and tune up your skills. Our rides follow one of the country’s premier biking routes, taking quiet roads to beautiful Oxford and then crossing the Tred Avon River via the small Oxford-Bellevue Ferry. We enjoy a beautiful boat ride along the Chesapeake Estuary, followed by a leisurely ride to Tilghman Island. We ride through the historic village of Unionville, by the “Little Red School House,” and enjoy a stunning day cycling through Blackwater National Wildlife Preserve, a haven for bald eagles, osprey and thousands of ducks and geese.

As further enticement, on Sunday, Monday, and Tuesday we enjoy waterfront views from our rooms at the Harbour Inn in historic Saint Michaels. Here, we enjoy wandering the streets lined with Colonial-era homes and elegant shops, strolling past the boat- lled marinas on the bay, and taking the included tour of the excellent Chesapeake Bay Maritime Museum. Then (and new for 2018) on Wednesday and Thursday we are guests at the spectacular Hyatt Regency Hotel Resort located right beside the Choptank River in Cambridge, Maryland. Every room offers a balcony or patio, and there are endless activities to indulge in while you explore this 400-acre estate.

Eastern Shore of Maryland Bike Tour Itinerary

DAY ONE  | 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. The town’s historic streets are lined with Colonial-era houses and shops, evidence that Saint Michaels has been a shipping and trading center since the 1630s.

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 so as to unwind after your day of cycling and sightseeing.

DAY TWO  |  Distance: 26 or 38 miles  |  Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier biking routes on the East Coast. We ride the bike path through Easton and then 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 crossing we ride pretty back roads through Royal Oak and Bellevue back to Saint Michaels.

DAY THREE  |  Distance: 18 miles  |  Terrain: Easier | Harbour Inn
This day is highlighted by a trip up the beautiful Miles River on Captain John’s cruiser, the Patriot. The narrated tour cruise takes us along a part of the Chesapeake Bay Estuary (the largest in the western hemisphere). This is a great way to learn about the history of the area, to view historic homes and wildlife, and watch local watermen harvest clams, oysters and the famous Chesapeake Bay blue crab during their respective seasons. Our afternoon options include a ride to Claiborne Landing, Cummings Creek and down to the fishing village on Tilghman’s Island. This is also a great opportunity to explore the fascinating Chesapeake Bay Maritime Museum where we can learn about the history of the bay, and its traditions in boat building, commercial fishing, yachting and navigation. There are twenty-three buildings here on eighteen acres with interactive exhibits, the popular Hooper Straight Lighthouse, and several historic vessels docked at the waterfront boat yard.

DAY FOUR  |  Distance: 38 or 48 miles  |  Terrain: Easier | Hyatt Regency Resort on Choptank River
On Wednesday our 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 visit 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. We picnic at Cordova Park and often take a beautiful optional ride to Kingston Landing before riding into Easton. Easton is often listed as one of the best small towns in America. It has lovely tree-lined streets, beautifully preserved Colonial and Victorian architecture, an arts and cultural center, sophisticated shopping, boutiques, and a renowned art gallery. After you explore Easton, we will transfer to Cambridge, Maryland and the spectacular Hyatt Regency Resort on the Choptank River.

DAY FIVE  |  Distance: 31 or 50 miles  |  Terrain: Easier | Hyatt Regency Resort on Choptank River
On Thursday we have a spectacular ride that takes us through the Blackwater National Wildlife Preserve. This 25,000 acre refuge was originally established in 1933 as a haven for ducks and geese migrating along the Atlantic Flyway (upwards of 35,000 geese and 15,000 ducks visit each year) and is host to one of the largest breeding populations of bald eagles on the East Coast. It is also a haven for several troubled species including the endangered Delmarva fox squirrel and the migrant peregrine falcon. Time magazine once called this refuge “nature on the throne of her glory”, and you will quickly understand why.

DAY SIX  |  Distance: 24 or 29 miles  |  Terrain: Easier
On our final day we take a shorter lovely ride cycling past old millponds and through mature wetland forests to the village of Trappe, ending our ride at Mitchum’s Market. This pleasant cafe is named after the movie actor Robert Mitchum and we can have a late morning coffee break here before our short shuttle back to Saint Michaels.

Eastern Shore of Maryland / Chesapeake Bay


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

reserveMay 6-11, 2018:  $2395
Reserve with $300 deposit

reserveMay 13-18, 2018:  $2395  
Reserve with $300 deposit

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

Single Supplement Fee: $350*

Default Supplement Fee: $175*

*Single Traveler? We are the most affordable tour company for single travelers, and our policies and rates are the very best. Please see our single traveler policies.

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.


logo-maryland-harbour-innSt. Michaels Harbour Inn, Marina & Spa is a year-round luxury resort, situated right off the Miles River, on the harbor in historic St. Michaels, on Maryland’s Eastern Shore.

An extraordinary experience awaits you at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, beautifully situated on the banks of the Choptank River. Discover the unparalleled services and amenities of this Chesapeake Bay resort, the most distinctive retreat on the Eastern Shore.

What’s Included

Boat excursion on the Chesapeake Estuary, Oxford ferry, tour of Blackwater Preserve, entry to Chesapeake Bay Maritime Museum, 5 nights lodging, 5 breakfasts, 4 dinners (you are on your own for dinner one night in Cambridge), bicycle and helmet. Free transfer provided from/to Easton, Maryland bus station/airport.


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