2009 Chesapeake Bay Bicycle Tour (6-Day)  
A bicycling vacation of the Eastern Shore of Maryland and Delaware

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

This 6 day vacation offers fully supported bicycling on all 6 days.  We spend 5 nights in charming Eastern Shore towns:  one each in historic Chestertown, MD, Lewes, DE, and Berlin, MD, and TWO in the picturesque waterfront town of St. Michaels, MD.

Day 1:  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.  We'll return to the inn for an orientation meeting over wine and cheese prior to a  gourmet dinner to satisfy the appetite you built today!

Day 2:  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 can either continue your bike journey east, or shuttle ahead to Lewes in the van. 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: Today, we bike along the coast and through several breathtaking salt marshes as we make our way south back into Maryland.  Our trip today ends with an afternoon at famous Assateague Island.  Walk on the beaches and watch the 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:  After a short morning shuttle, we make our way today to 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 wharves to watch the local fishermen unload their catches of crabs and oysters.  Our inn this evening, the Old Brick Inn, welcomes us with handmade truffles from the Scottish Highland Creamery.  We again relax before our last dinner as a group this evening at a local gourmet favorite.

Day 5:  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:  Rising early, we start with a short morning shuttle after breakfast before making our way back to Chestertown in the early afternoon.  More lovely back roads take us from St. Michaels east and then north 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.

	Lodging: 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.
	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.
	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.
	Nights 4 & 5:  The Old Brick Inn, St. Michaels, MD.  In the tradition of fine country inns, The Old Brick Inn offers the European charm of a boutique hotel.  Whether it's Banana's Foster French Toast, Baked Eggs with Fresh Asparagus & Crab, or maybe Fresh Raspberry Crepes, you can be assured that we will be well fueled for our day's excursion.

Extend Your Vacation:  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.   

Call 888.251.3206 (local number is 336.794.1054) or click here to make your reservation today!

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Hatteras Light photo courtesy of North Carolina Division of Tourism, Film and Sports Development

Carolina Tailwinds   P.O. Box 24716   Winston-Salem, NC 27114-4716   888.251.3206 or 336.794.1054 
email: info@CarolinaTailwinds.com