Maryland Eastern Shore - Northern

Maryland Eastern Shore - Northern

4 Day Inn Tour

Tour Information

Date: 05/12/17 - 05/15/17
Meet: Chestertown, MD
Time: 2:30pm
Tour Price: $1450
Single Upgrade: $300

Our Maryland Eastern Shore tour features flat, quiet back roads surrounded by the Chesapeake Bay. We bike past rich tidal marshes, freshwater ponds and lots of farmland with rows of corn and wheat. We promise flat terrain and ocean views, quaint towns and a gorgeous inn.

Call Us!

The tour is filled, but call us. We may be able to squeeze you in.





Flat terrain. Beginner to moderate cycling level.

3 nights lodging, 3 breakfasts, 3 picnic lunches, 3 dinners, snacks, kayaking, detailed cue sheets, van support & trained guides.


Maryland Eastern Shore - Northern

Accommodations are subject to minor changes. 

Great Oak Manor

Fly into and out of the Baltimore-Washington International Airport. Or take the train. WomanTours will provide a shuttle to and from the airport/train station for $30 each way. Or drive directly to our inn in Chestertown, MD.

Cy Pugh

Cy Pugh
Tour Leader

"I had a GREAT time on the tour! This was my first tour and it exceeded my expectations! Great Oak is truly a wonderful place to stay! And the staff there made us feel both instantly “at home” and treated “like royalty”. I did not want for anything!!! All of our meals were scrumptious!!! We had lots of choices and everything was homemade fresh with the best ingredients. I had been quite sick just 10 days prior to the tour and I was unsure how I would fare on this, my first tour. I ended up needing the services of the sag wagon when I just could not pedal another stroke. I’d turn around and there was either Kelly or Sid behind the wheel of the sag wagon, ready to take me forward to home base. I did not need any assistance the last 2 days we rode - I was already stronger!!"

Mo K. Haverhill, MA

Tour Itinerary

DAY 1: Meet at the Great Oak Manor Inn in Chestertown, MD at 2:30pm for our orientation. Come dressed to ride. Then we’ll have a bike fitting and our first bike ride together.

We’ll bike south along the meandering flat roads of the Eastern Shore to St. Paul’s Episcopal Church, a parish founded in 1693. The present building is from 1713 and once served as the barracks for British troops during the War of 1812. Be sure to check out the giant oak trees in the yard, believed to be more than three centuries old.

Once back at the inn, we’ll enjoy our first dinner together. Situated on the Chesapeake Bay, the Great Oak Manor will be our home during the tour. It looks elegant — almost regal — in its secluded spot overlooking the water. We’ll have the place to ourselves and we promise that you probably won’t want to go home. 20 miles.

DAY 2: After a hearty breakfast, we’ll head north for our second bike ride toward the small town of Betterton. Located where the Sassafras River flows into the Chesapeake Bay, this historic town is filled with old Victorian homes and resorts built for the steamboat passengers at the turn of the last century.

If you’re feeling especially energetic, you can bike the optional10-mile loop to Turner Creek Wharf. Look for a Great Blue Heron or a Canadian Snow Goose at this pretty spot on the Sassafras River.

Then we’ll have a picnic lunch at Betterton Beach. If it’s warm enough, you can even go for a swim. The water isn’t very salty. Once back at the inn, we’ll have dinner together and celebrate anyone who has accomplished a “personal best” by cycling more miles than ever before. 30 — 57 miles.

For dinner, we head into the 18th century town of Chestertown. Steeped in history, the town had its own Tea Party in 1774, and is also the home of Washington College, one of the oldest colleges in the nation.

DAY 3: Today, we head out on our bikes for a short trip to the bay. Once there, we’ll trade our bicycles for kayaks. The gentle waters are perfect for first-time kayakers. We’ll paddle through protected tidal areas, stopping at Davis Creek and Long Cove Landing to look for kingfishers, osprey and bald eagles.

Once back on land, we’ll enjoy a picnic lunch before getting on our bikes to head back to our inn. Then you can curl up on a porch chair overlooking the bay before our last dinner together. 22 miles.

DAY 4: After our last sumptuous breakfast, we’ll explore more of the quiet back roads of Kent County, cycling through forests and farmland to the African American Schoolhouse Museum. Built in 1890, the one-room schoolhouse is full of photographs, oral histories and artifacts of the lives and contributions of the county’s African American community.

Finally we’ll return to our inn for a picnic lunch and to say our good-byes. The shuttle will leave at 1:00pm for a 3:00pm arrival at the Baltimore airport/train station. 20 miles.