Maryland Eastern Shore

DAY 5: Enjoy your morning exploring charming Easton. Full of tree-lined, narrow streets, it is fascinating to walk among the cute shops, art galleries and restaurants. Easton also features the premiere Academy Art Museum and a Historical Society Museum. You’ll meet the women who have arrived for the second half of our tour at 2:00pm at the orientation. Come dressed to ride.

The afternoon bike ride takes us to Unionville, a community settled by ex-slaves after the Civil War. It’s a beautiful ride, with a canopy of trees above most of the roads to keep us cool. We’ll cross a small drawbridge and an even smaller wooden bridge. 18 miles.

DAY 6: Today, we’ll explore the Blackwater National Wildlife Refuge by bicycle. We’ll begin at the Visitors Center, bike through the refuge and then through Upper and Middle Hooper Islands.

The Blackwater National Wildlife Refuge’s 23,000 acres were established as a park for migratory birds in 1933. Its rich tidal marshes, freshwater ponds, and mixed evergreen forests serve as home to the 35,000 geese and 15,000 ducks that fly by at the peak of fall migration every November.

The Refuge is also a haven for three threatened or endangered species, including the bald eagle, the Delmarva Fox squirrel and the peregrine falcon. And if we’re lucky, we may see some white-tailed fawns or some eaglets starting to fledge. Bring your binoculars!

We’ll have a picnic lunch on the road during the ride and then we’ll have dinner together tonight in Easton. We’ll be sure to celebrate anyone who has accomplished another “personal best” today. 27, 37 or 61 miles.

DAY 7: Today we head south and west to explore farmland, the coastline and the charming town of Oxford where James Michener wrote most of his book Chesapeake. From there, we’ll take a short ferry ride across the bay to St. Michaels for lunch on your own. Consider having crab cakes, which are famous in this area. You can take the time to visit the Chesapeake Bay Maritime Museum or shop along Main Street before cycling back to Easton. 33 or 45 miles.

DAY 8: After a last hearty breakfast, we’ll explore more of the quiet back roads around Easton and head to the Little Red Schoolhouse, circa 1885.

We’ll return to Easton for a picnic lunch and to say our good-byes. The airport shuttle will leave at 1:00pm for a 2:30pm arrival at the Baltimore airport to catch an airplane or train. 21 miles.

This tour combines our two other shorter Maryland tours into one long one and gives you a discount. We’ll shuttle you between the two tours and provide you with an extra night of lodging. You’ll know you’ve seen the best the Maryland Eastern Shore has to offer, and a full week of cycling will surely get you into great shape!

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. 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.

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.

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. 30 — 57 miles.

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 relax on the porch overlooking the bay before dinner at the inn together. 22 miles.

DAY 4: 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.

After returning to our inn for a picnic lunch, we’ll say good-bye to the women who have chosen to do only the first half of the tour. WomanTours will provide a shuttle to the Tidewater Inn in Easton, MD, or drive if you have your own vehicle. Dinner is on your own tonight. 21 miles.