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Maryland Bay to Beach

  • Harbor sunset
  • Wetland biking
  • Red-winged blackbird
  • Steamed crab
  • Harriet Tubman Museum
  • Assateague Island pony
DURATION
6 Day(s)
DAILY BIKING
9 to 50 miles
TRIP DIFFICULTY
1-Easier
STARTING FROM
$2695
SINGLES FROM
$600

Trip Overview

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.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
St. Michaels 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 2 - Easton and the Oxford-Bellevue Ferry
Distance: 26 or 38 miles | Terrain: Easier | Harbour Inn
On this tour we treat you to what is considered one of the premier coastal 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 3 - Tilghman's Island & Maritime History
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 4 - Wildlife Refuge & Harriet Tubman History
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 5 - Snow Hill & Assateague Island
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 6 - Departure Day
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.

Map

Picture of Maryland Bay to Beach

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start End Cost Availability
May 03, 2020 May 08, 2020 $2695.00 Available! Reserve Reserve
May 10, 2020 May 15, 2020 $2695.00 Available! Reserve Reserve
Oct 04, 2020 Oct 09, 2020 $2695.00 Available! Reserve Reserve
Oct 11, 2020 Oct 16, 2020 $2695.00 Available! Reserve Reserve

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. Airfare not included.

Dates & Pricing

Make your reservation with confidence. Your tour is completely 100% refundable until the final payment due date.

Start: May 03, 2020
End: May 08, 2020
Cost: $2695.00
Availability: Available!
Reserve
Start: May 10, 2020
End: May 15, 2020
Cost: $2695.00
Availability: Available!
Reserve
Start: Oct 04, 2020
End: Oct 09, 2020
Cost: $2695.00
Availability: Available!
Reserve
Start: Oct 11, 2020
End: Oct 16, 2020
Cost: $2695.00
Availability: Available!
Reserve

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. Airfare not included.

Inns

Where you stay along the way.

St. Michaels Harbour Inn
St. 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 Atlantic Hotel
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.

Gallery

Images from this tour. Click each to see it larger.

Harbor sunset Wetland biking Red-winged blackbird Steamed crab Harriet Tubman Museum Assateague Island pony