Maryland > Bay to Beach (NEW route!)

Oct. 13-18, 2019
2020 Dates: May 10-15, May 17-22, October 4-9, October 11-16, 2020

Celebrate spring or fall 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 10 best places to tour in North America. The roads are gently rolling as we wind our way through the Chesapeake estuary and its small bays and inlets. We offer additional riding for the energetic, so this is a perfect tour to 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. Ride to the tip of Tilghman Island, with a great local lunch. On Wednesday, enjoy a stunning day cycling through Blackwater National Wildlife Refuge, a haven for bald eagles, osprey and thousands of ducks and geese. Then we’ll spend Thursday and Friday exploring the ocean side of the peninsula, including visiting the ponies at Assateague Island National Seashore.

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-lined marinas on the bay, and taking the included tour of the excellent Chesapeake Bay Maritime Museum. Then we move to charming Berlin, Maryland, and the historic Atlantic Hotel.

Maryland Bay to Beach Bike Tour Itinerary

DAY ONE  | Arrival Day | Harbour Inn
We begin our tour in Saint Michaels, a quaint waterfront village situated on a picturesque peninsula between Tilghman Island and Easton. It’s 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 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 to the end of Tilghman’s Island through estuaries, farm fields and the view across the Chesapeake Bay. Crossing the drawbridge on Tilghman’s Island, you arrive on one of the Chesapeake’s iconic locations, where fishing and crabbing are still a way of life. Have lunch at Two If By Sea, and take time to explore the history- and Bay-themed bookstore next door. Return to Saint Michaels by van to enjoy more corners of the peninsula. And visit 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 23 buildings here on 18 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 | The Atlantic Hotel
On Wednesday, we have a spectacular ride that takes us through the Blackwater National Wildlife Refuge. This 25,000 acre preserve 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. We also stop in the recently established Harriett Tubman Underground Railroad National Historical Park, touring the well-designed visitor center and seeing several historic sites. We end the day with a transfer to Berlin, Maryland, and the Atlantic Hotel. Scenic Berlin has 47 structures on the National Register of Historic Places (including our hotel) and has served as the backdrop for movies such as Runaway Bride and Tuck Everlasting.

DAY FIVE  |  Distance: 31 or 50 miles  |  Terrain: Easier | The Atlantic Hotel
On Thursday, we ride a loop to Snow Hill, Maryland, where we enjoy lunch at another historic riverside town. After lunch, we’ll head back toward Berlin and out to Assateague Island for an afternoon walk along the beach and visits with the famous Assateague ponies. You can bike or van after lunch, and the evening will end with a celebration dinner in Berlin at the Atlantic Hotel. There will also be time to visit one of Maryland’s best craft breweries, Burley Oak.

DAY SIX  |  Distance: 24 or 29 miles  |  Terrain: Easier
On our final day, we take a lovely early morning ride or van trip back out to Assateague for the sunrise over the Atlantic, if you are an early riser. Riders can enjoy a final morning of relaxed distances or a longer ride along the coastal area before our shuttle back to Saint Michaels.

Maryland Bay to Beach Tour / Chesapeake Bay


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

reserveOctober 13-18, 2019:  $2395  
Reserve with $300 deposit

reserveMay 10-15, 2020:  $2395  
Reserve with $500 deposit

reserveMay 17-22, 2020:  $2395  
Reserve with $500 deposit

reserveOctober 4-9, 2020:  $2395  
Reserve with $500 deposit

reserveOctober 11-16, 2020:  $2395  
Reserve with $500 deposit

Final payment due 90 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee: $350*

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

  • If you cancel 90 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 60 and 89 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 59 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.

The historic Atlantic Hotel has served the town of Berlin for the past 120 years with outstanding cuisine, gracious service and upscale accommodations in Victorian-period style.


What’s Included

Oxford ferry, tour of Blackwater Preserve, entry to Chesapeake Bay Maritime Museum, 5 nights’ lodging, 5 breakfasts, 1 lunch, 4 dinners (you are on your own for dinner one night in Berlin), 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