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Biking Vacation Maryland: Cycling the Chesapeake Bay​

Activity Level: Easy  |  Daily Mileage: 13 – 32 mi  |  Daily Biking: 2 – 4 1/2 hr
Land only
6 days from only
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Detailed Itinerary

Day 1 - Arrive Easton / Warm-up ride / Welcome reception

Make your own arrangements for travel to Maryland. If you're flying to Baltimore, VBT will offer a shuttle from the Baltimore-Washington International Airport (BWI). The shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 1:00 pm. Shuttle reservations are not required or available. The shuttle will depart from the lower level, the baggage claim level, at Door 10 on the inner roadway. Your shuttle bus will carry “GO The Airport Shuttle” titles, and the driver will be holding a VBT sign.

If you are scheduled to arrive at the airport after 1:00 pm or are delayed, you must take a taxi or bus at your own expense. If you are driving to the tour, we recommend that you leave your vehicle in Easton while on tour. You can park at the Tidewater Inn while on tour (Sunday through Thursday nights inclusive). You may return to this location at the end of the tour by way of the VBT van.

If you are delayed or your travel plans change, please contact the first inn; they will pass your message to your VBT Trip Leaders.

Our group meets at the Tidewater Inn to begin your Maryland vacation. After settling in, explore the village from the hotel's central location. At 3:00 pm, join your VBT Trip Leaders for a safety and bike-fitting session, followed by a short warm-up ride. At 5:00 pm, meet up with the group for an orientation and welcome reception before a 7:00 pm dinner at the inn.

Day 2 - Ride the Oxford & St. Michaels Trail / Lunch in St. Michaels / Guided visit to the Chesapeake Bay Maritime Museum

Today you are in for a treat. The Oxford/St. Michaels loop is considered one of the premiere biking routes on the east coast. We ride a counter-clockwise route from our inn, stopping for an included lunch in St. Michaels, a small bayside town on a long, narrow neck of land. Afterward, our group will have a self-guided tour of the impressive Chesapeake Bay Maritime Museum. The museum comprises more than ten exhibit buildings, the 1879 Hooper Strait Lighthouse, a working boatyard and the world's largest collection of Bay boats. Plus, St. Michaels offers wonderful shopping, snacking and plenty of people watching opportunities. 

After our visit in St. Michaels, we’ll hop back on our bikes, riding through Royal Oak to reach Bellevue. Upon arrival, we'll board the modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America. After crossing, we'll be in Oxford. Worth a stop, this 17th-century town has a long tradition of boat building. Don't forget to stop for homemade ice cream! The Scottish Highland Creamery is the place for it.
After your mid-afternoon ice cream delight, continue back to our inn. Easton has been featured on many “best small towns in America” lists. The village is small in scale, but packed with great dining, antiques, galleries and shopping. Our comfortable inn has played a central role in the village since 1712. Recently renovated, it features great eating and drinking at Hunters' Tavern.

For dinner, choose from one of the fine restaurants in town. 

Day 3 - Ride the farmlands of Talbot County / Cordova / Dairy visit and hand-crafted cheese tasting

More than half of the land in Talbot County is devoted to farming and we’ll spend the morning riding through its wide-open agricultural terrain.  
We divert from the rows of wheat, corn and soybeans, riding on shaded lanes leading down to rewarding views of the Choptank River. Stop at Kingston Landing for a relaxing respite. The river’s edge is an active birding area and you may spot Bald Eagles, Yellow-throated Warblers or Indigo Buntings.  

Later, we’ll ride on to the sleepy town of Cordova. You might enjoy exploring the town’s two general stores before we turn west, riding back towards Easton. En route to our inn, we’ll stop for a picnic lunch on the grounds of a family run farm. After our picnic, we’ll meet Eric and Holly and their grass-fed girls for an introduction into the dairy operation at work. Before hitting the road, we sample the artisanal cheeses and other products made here at Chapel’s Country Creamery.

Tonight's dinner is at one of Easton's popular restaurants. 

Day 4 - Sail to Rock Hall / Eastern Neck Island National Wildlife Refuge

This morning, board the HM Krentz for a sail north through the Kent Narrows to Rock Hall. Our skipper, Captain Ed, has spent more than 35 years dredging oysters and sailing skipjacks for his livelihood and his boat, the HM Krentz, is a broad-beamed former working skipjack. Her stable decks are perfect for catching sea air. 

On arrival in Rock Hall, we'll enjoy a picnic lunch before cycling to the Eastern Neck Wildlife Refuge. A glorious haven for more than 240 bird species, you might want to take a walk along the wooden Tubby Cove Boardwalk, which extends over the marsh to a wooded island. Once on the island, the boardwalk continues to two viewing platforms, and a rough walking trail off the main path ends at an elevated viewing platform that provides vistas of Chesapeake Bay and into Tubby Cove and Calf Pasture Cove. After exploring, we'll continue our ride to the inn, where a swim in the pool and a cool drink on the dock may be in order. Our hosts Jim and Joanne welcome us. Dinner is on your own tonight in one of Rock Hall's restaurants.

Day 5 - Ride to Chestertown

We ride north today to Chestertown, an historic colonial town located on the Chester River. Chestertown was founded in 1705, and became one of Maryland's six Royal Ports of Entry, and in the mid-eighteenth century it was the second leading port in Maryland. With this important designation and the resulting shipping business, the town became quite wealthy, as heralded by the brick mansions and townhouses along the waterfront. Your leaders will offer you a self-guided cycling tour of the historic section of Chestertown. 

Continue exploring along the town's brick sidewalks, visiting shops and galleries along the way. While you're in Chestertown, take the time to enjoy lunch on your own at a local cafe, the bakery or one of the town's numerous restaurants. Your leaders will provide you with some great recommendations.

If you prefer a non-riding option today, you may spend the day at the inn, or enjoy browsing the charming shops and relaxing in the cafes in Rock Hall.

Tonight, we gather to celebrate with a festive farewell dinner.

Day 6 - Depart for home

Our tour concludes after breakfast at our inn. Our included shuttle is available to take you back to the Baltimore-Washington International Airport (BWI), arriving around 12:00 pm. We suggest a flight out of BWI no earlier than 2:00 pm. We will shuttle guests who have cars parked at the Tidewater Inn. This shuttle will arrive at the inn around 12:00 pm.

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