Chesapeake Bay Tour

Bike Tour of Maryland's Eastern Shore

A Six Day Cycling Vacation on the Lovely Eastern Shore of Maryland

Miles of flat coastal cycling await you in this pristine region defined by the numerous tidal rivers that drain into the Chesapeake Bay and the shimmering beauty of undeveloped seashore on the Atlantic Ocean. Views of rural farmland, Chesapeake Bay skipjacks and sailing craft, fishing boats, and quaint communities greet you along the way. 

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Chesapeake Bay

Chestertown, MD

Tour Difficulty

Flat, Easy Terrain


6 Days, 5 Nights


Brampton Inn

Nearest Airport

BWI Thurgood Marshall Airport


From $2275 per person


5/3/20 - 5/8/20 9/27/20 - 10/2/20
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Day 1

22–45 miles, flat

We meet in Chestertown, MD at the Brampton Inn, a quiet getaway minutes away from downtown Chestertown.  Arrive early to spend some time in this historic town, founded in 1706, on the banks of the Chester River.  At 1:00 p.m., we will take a bike tour of the scenic back roads of Kent County.  We are never far from the mighty Chesapeake Bay, and glimpses of its sparkling waters are numerous.  We pay a visit to the old watermen's' town of Rock Hall on the banks of the Chesapeake.  After pedaling back to the inn, we'll have an orientation meeting over wine and cheese prior to a  gourmet dinner to satisfy the appetite you built today!

Day 2

25–57 miles, flat

This morning, we savor one of the Brampton's famous breakfasts (preview a sample menu: (click here) before biking away from Chestertown.  We make our way south toward the ocean via the quiet farm roads of Maryland and Delaware, with a stop along the way for a catered picnic lunch.  After lunch, you may bike on to Lewes. Optional activities in Lewes include walking the streets of the historic district settled by the Dutch in the 17th century, visiting nearby Cape Henlopen State Park with its undeveloped beaches, or simply relaxing on the balcony of your room overlooking the Lewes waterfront. Lodging is the Inn at Canal Square with plenty of time this evening to explore the side streets and local restaurants on your own.

Day 3

25–66 miles, flat

Today we bike from Lewes to nearby Rehoboth Beach, then south along the Delaware coast.  Turning inland, we'll make our way past rural farms and salt marsh as we make our way back into Maryland.  After lunch in Berlin, MD, you may opt today to bike toward famous Assateague Island.  At the state park there, you can walk on the beach and see wild ponies graze on the marsh and dune grasses.  Descendants of a herd that grazed here in the 17th century, the ponies are the island's only residents in addition to the deer and elk herds.  We end our journey today in the small town of Berlin, MD.  The brick storefronts, shady side streets and embellished facades of the mostly 19th & 20th century buildings create a pleasant streetscape.  Relax in the rocking chairs on the front porch of our inn, the Atlantic Hotel.   We'll recap the day’s adventures over wine and cheese prior to another gourmet dinner as a group this evening.

Day 4

29–55 miles, flat

Making our way back toward the west today, we'll enjoy the picturesque country roads of Wicomico, Dorchester and Talbot Counties.  A brief side trip through the small town of Oxford ends with a ferry ride across the Tred Avon River.  We reach our end destination of St. Michaels, one of the most charming villages on the Eastern Shore and the oldest town in Talbot County.  Wander down to the town harbor and marina to see fishing boats sailing yachts, and a historic Skipjack.  Our inn this evening, the Harbour Inn, is located on the marina in the heart of historic St. Michaels.  We again relax before our last dinner as a group this evening at a local gourmet favorite.

Day 5

0–50 miles, flat

You get the chance to have a day off the bike today.  St. Michaels offers so many opportunities, you won't be bored!  Boutique shops, day spas, and a renowned Maritime Museum are all within walking distance.  If you prefer to bike, join us on a ride to Tilghman Island ("the pearl of the Chesapeake") and back.  Tilghman's quiet pace and scenic harbors will charm you.  And don't miss the crab cakes at Bay 100!

Day 6

32–54 miles, flat

Rising early, we'll bike away from St. Michaels after breakfast, making our way back to Chestertown in the early afternoon.  More lovely back roads take us past beautifully maintained farms and equestrian estates.  Past through a couple more quaint Eastern Shore town centers before re-entering Chestertown on the way to Brampton Inn.  One final catered lunch together and showers are provided prior to departure.  Danielle at Brampton Inn has even named the chili she frequently serves on this last day in honor of our groups -- Carolina Turkey Chili.  See here recipe here:  (click).   Thanks Danielle, we love it!


$2,275 - $2,375
Bike Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


5 nights at boutique inns


Dinner on Nights 1, 3, & 5; All lunches except 1; All breakfasts; Snacks; and hors d'eourves most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Transfer from Annapolis, MD

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 in the Annapolis, MD area, located approximately 25 miles from Baltimore, MD (BWI) airport, for transfer to our tour start location in Chestertown, MD.  Timing formally coordinated 2 weeks prior to tour date but typically takes place around 10 – 10:30 a.m. on the morning of day 1.

More details on what's included: 

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Brampton Inn, Chestertown, MD

Night 1

Brampton Inn, Chestertown, MD.  Located on 20 acres of woodland and gardens, the Branpton Inn has been described by the NY Times as "...meticulously restored, utterly quiet, in a pastoral setting.  The perfect base for exploring the Eastern Shore."  You may want to add a night here to the beginning or end or your tour.

Inn at Canal Square, Lewes, DE

Night 2

The Inn at Canal Square, Lewes, DE.  Located on the waterfront in the heart of Historic Lewes, The Inn at Canal Square offers its guests comfort coupled with seaside charm.  

Atlantic Hotel, Berlin, MD

Night 3

The Atlantic Hotel, Berlin, MD.  Each room is beautifully furnished with antiques and unique in its decor. Rich green and burgundy, delicate rose and aqua, and deep mahogany tones all help transport you to a gentler time and quieter place.

View from Saint Michaels Harbour Inn

Nights 4 & 5

The Harbour Inn, St. Michaels, MD.  All of our rooms are waterfront, overlooking the beautiful St. Michaels Marina.  Amenities include an outdoor pool, spa, and local area shuttle.  The open air Harbourside Grill is a great place to relax over a beverage at the end of the day.



The terrain is flat, making it accessible to all ability levels.  Strong coastal winds sometimes present a minor challenge, but they are just as likely to propel us along our route!  Along the way, observe coastal wetlands and rural farmland as we bike the scenic back roads of Maryland and Delaware.  Because the route distance options are so flexible, this is one of the best tours for bicycling companions of differing riding styles.

This 6 day tour offers routes of 25 - 50+ miles each day (at your option).  Stronger cyclists may bike over 50 miles on each day of the tour, including up to 75 on two days.  Less ambitious cyclists take advantage of short cuts and quick "leap frog" van shuttles along the route to tailor the route to their needs. 

Tour Point of Origin:

Brampton Inn, 25227 Chestertown Rd, Chestertown, MD  (410) 778-1860

Getting To The Tour Start (Chestertown, MD):

Driving:  Approximate travel time to the Brampton Inn:

  • Wilmington, DE: 1 hr. 10 min.
  • Baltimore, MD: 1 hr. 30 min.
  • Annapolis, MD: 1 hr.
  • New York, NY: 3 hrs. 45 min
  • Philadelphia, PA: 1 hr 30 min.
  • Washington, DC  1 hr. 45min.

Baltimore/Washington International Airport (BWI) is approximately 62 miles away.  It is served by most major airlines.  You may want to arrive the evening prior to the tour and stay overnight in the Annapolis or Baltimore area.  Airport shuttles conveniently serve both cities.  We can provide a complimentary shuttle from/to Annapolis, MD the first morning of the tour.  Contact us for more details.

Philadelphia International Airport (PHL) is approximately 73.5 miles away.  It is served by most major airlines.  Shuttle service to Chestertown can be arranged, and car rental agencies are available. 

Reagan National Airport (DCA) is approximately 79 miles away.  It is served by most major airlines, and car rental agencies are available. 

Dulles International Airport (IAD) is approximately 106 miles away.  It is served by most major airlines, and car rental agencies are available.

Ground Transit:  With advance coordination, Carolina Tailwinds can provide airport shuttle from/to Annapolis.  Call us to coordinate timing.  Otherwise, several shuttle services and car rental agencies are available.  Call us for details.

Arrival/Departure Timing

Arrival time of the first day of the tour is flexible.  Try to arrive no later than 11:30 a.m., ready to ride or ready to change quickly into bike clothes. That means an early morning arrival at BWI.   Departure time from Chestertown on the last day is between 1-3 p.m.  Your return flight should not be scheduled any earlier than 6:30 p.m.

Extend Your Stay

Before or after our activity packed tour, you may want to tack on a few days. 

Perhaps in the vibrant historic district of Annapolis.  Or continue your visit of the coast by driving down to the Virginia portion of the Eastern Shore to Onancock, Tangier Island, or Cape Charles.  There is plenty to see and do in Maryland and eastern Virginia.  We'll be happy to make suggestions for you and help with arrangements.

The Chestertown Area:   There is a lot to do in and around Chestertown if you have time.  Kent County offers some of the best biking on the Eastern Shore.  Though we will take advantage of the southern county roads while on tour with us, the northern county roads are well worth exploration as well.  We can recommend a bike route should you arrive early.  

Also, Winterthur, the famous DuPont estate, is located 1.5 hours northeast of Chestertown in Delaware. The former home of Henry Francis du Pont (1880-1969) is full of the most spectacular collection of American furniture and decorative arts anywhere in the world.  The surrounding 60 acre estate gardens are also renowned for their breathtaking beauty.

Shoppers will enjoy downtown Chestertown's many and diverse shops in a walkable, pleasant environment.  Antique shops abound in this area which is known for the nearby Crumpton Auction Sale held year round every Wednesday.


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