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St. Michaels Weekend Bike Tour

  • Tandem near Tilghman Island
  • Oxford ferry sign
  • Oxford ferry
  • Harbor
  • bald eagle
  • Steamed crabs
DURATION
3 Day(s)
DAILY BIKING
17 to 45 miles
TRIP DIFFICULTY
1-Easier
REVIEWS
STARTING FROM
$995
SINGLES ADD FROM
$400

Trip Overview

Celebrate spring or savor the fall with a weekend of easy coastal riding on quiet roads. Visit a fascinating variety of historic Tidewater Maryland villages on your bike tour 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.

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
St. Michaels 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.
DAY 2 - Charming Tree-lined Villages
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.
DAY 3 - Departure Day
Distance: 27 miles (with shorter option)| Terrain: Easier
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.

Map

Picture of St. Michaels Weekend Bike Tour

Dates & Pricing

Prices are based on double occupancy. Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start End Cost Availability
Oct 16, 2020 Oct 18, 2020 $995.00 Available! Reserve Reserve

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. Airfare is not included.

Dates & Pricing

Prices are based on double occupancy. Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start: Oct 16, 2020
End: Oct 18, 2020
Cost: $995.00
Availability: Available!
Reserve

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. Airfare is not included.

Inns

Where you stay along the way.

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

Guests say …

Quotes from guests about this tour:

 

"Lovely bike route, friendly trip leaders, great location, nice bikes."

Lisa and Patrick E.


"Everything was very well organized, and the communication was good before and during the trip."

Louise C.


"Both Wayne and Kate are friendly, smart, and attentive people, with fun personalities. I enjoyed having meals with them, talking to them, etc. Wayne got me set up quickly on my bike. That said, it was clear from several aspects of the trip that this was a new company and that all the kinks had not been worked out."

Lisa and Patrick E.


"Enthusiastic, diligent workers, pleasant to spend time with!"

Nancy S.

Gallery

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

Tandem near Tilghman Island Oxford ferry sign Oxford ferry Harbor bald eagle Steamed crabs