Maryland Eastern Shore - Southern - Bike Tour

Maryland Eastern Shore - Southern - Bike Tour

4 Day Hub & Spoke Inn Bike Tour

Tour Information

Date: 05/03/25 - 05/06/25
Meet: Easton, MD
Time: 2:00pm
Tour Price: $2150
Single Upgrade: $700

Discover this bicycling mecca of flat, quiet, back roads on the Eastern Shore of Maryland. Full of history and beauty, this area makes for some wonderful spring cycling. We'll stay in one hotel during the entire time of this Hub and Spoke Bicycle Tour.

5% Discount

The first 6 women to sign up receive 5% discounts.





Flat terrain on paved bike paths and quiet roads. Leisurely to moderate cycling level.

3 nights lodging, 3 breakfasts, 2 picnic lunches, 3 dinners, snacks, digital maps, and GPS files, van support, and trained guides.

$195 for a Cannondale Quick 3 hybrid or Cannondale Topstone 2 adventure road bike; $350 for a Gazelle T10 Ultimate low-step e-bike or Specialized Vado step-thru e-bike.





Accommodations are subject to minor changes. 

Hampton Inn Easton

Fly into and out of the Baltimore-Washington International Airport (BWI). Or take the train. WomanTours will provide a shuttle to and from the airport/train station for $75 each way. Or drive directly to our inn in Easton, MD.


How do I sign up?

You can Register / Sign-up for a Tour online. Or call our office at 585-424-2124 to do it over the phone, Monday - Friday, 9:00-5:00 Eastern Time. We’ll need a Visa, MasterCard or Discover number or a check for the deposit. If you sign up within 30 days of the start of the tour, we require payment in full. Then we’ll send you a tour confirmation packet with many more details about your trip, including travel arrangements, a packing list and an optional training schedule. Most of our tours fill completely and have waiting lists, so don’t wait too long before deciding to join us!

What about electric-assist bikes (e-bikes)?

Electric-assist bikes - or e-bikes - have quiet, battery-powered motors that add power to your pedalng. They increase your speed and assist you in cycling up hills. Most e-bikes have a range of assistance, so you can choose how much of a boost you'd like. E-bikes make it easier to do all the miles in all types of terrain. We allow electric-assist bicycles on our tours if you'd like to bring your own. We also have e-bikes available for rent on most of our trips -- look for the e-bike symbol. We do not make e-bike recommendations if you're considering purchasing your own. We suggest you rent one on a tour first so you can try it!

I am coming alone on this tour. Will I be the only one traveling alone?

Absolutely not. Many of our participants come by themselves. That is part of the reason for the existence of WomanTours--to provide women with riding partners as well as scenic vistas and interesting tours.

Can I bring my own bike?

About half of our guests bring their own bicycles. Cross-country cyclists must ride their own bikes. Upon signing up for a tour, you will receive information for packing, shipping and flying with your bike.

What about the rental bikes?

We have a fleet of women-specific bicycles available for rent for $195 for most tours in the U.S. We will need your height and inseam measurement to fit you properly. You can choose a hybrid bike with straight handlebars or an adventure road bike with racing-style drop handlebars. We also have electric-assist bikes, Gazelle T10 or the Specialized Vado, available for $350 for most tours. Our rental bicycles have a phone holder, back rack, water bottle holders, and back bag.

Will I be the oldest (or youngest) woman on the tour?

Probably not! We’ve had women as young as 18 and as old as 86. The average age of our guests is 56 on our shorter tours and 60 on our cross-country tours.

What if I have to cancel a tour within the USA?

We understand that personal circumstances sometimes force women to cancel their travel plans. Therefore, we have tried to be as generous as possible with the following domestic tour cancellation policy for our regular tours:

  • 75+ days before tour departure: forfeit $150 of your deposit.
  • 50 - 74 days before tour departure: forfeit 25% of the complete tour price.
  • 30 - 49 days before tour departure: forfeit 65% of the complete tour price
  • 15 - 29 days before tour departure: forfeit 85% of the complete tour price.
  • 0 - 14 days before tour departure: forfeit 100% of the complete tour price.
  • No refunds are possible after the tour begins.

In addition, you may transfer $350 to another trip up to 75 days before departure. On domestic US trips (excluding Alaska,) you may also transfer 50% of the trip price, less $50 up to 30 days before departure. WomanTours will hold any “transfer funds” on account through December 31 of the following year. Any money left on account beyond this deadline will be forfeited.

Please note that our cross-country and epic tours have their own cancellation policies, depending on the tour's payment schedule. The $300 registration fee for these tours is nonrefundable and nontransferable.

"We had meetings each morning that described our day and we knew what to do and how long we had. It was always comforting to have the guides sweeping back and forth with the van. I always felt that we were in contact and comfortable when we were out there."

Pat B. Victor, NY

Maryland Bike Tour Itinerary

DAY 1: Meet at our starting hotel in Easton, MD at 2:00pm for our orientation dressed to ride. We’ll have a bike fitting and our first bicycle ride. Then after a quick shower, we’ll have dinner together.

We are a short walk from the center of charming Easton, one of the Top Ten Best Small Towns in America. Full of tree-lined narrow streets, it’s fun to walk among the cute shops, art galleries and restaurants.

Our first leisurely bike ride will take us to Unionville, believed to be the only community settled by formerly enslaved soldiers. After the Civil War, veterans of the Union Army’s Colored Troops were leased farmland by a local Quaker man so they could settle here. We’ll cycle by the St. Stephens AME Church where the 18 founders are buried today.   

It's a beautiful ride, made richer by the history that happened here. The abolitionist Frederick Douglas was enslaved in the area. Harriet Tubman led countless slaves to their freedom through here. We'll cycle with a canopy of trees above us, crossing a small drawbridge and an even smaller wooden bridge, reminders of a time not so long ago. 20 miles ±185'.

DAY 2: 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. Look for the Hooper Island Lighthouse three miles off shore.

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. If we’re lucky, we may see some white-tailed fawns so 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 a “personal best” today by cycling more miles than ever before. 35 or 59 miles, ±183' or ±303'.

DAY 3: Today we head south and west to explore farmland, the coastline and one of the oldest towns in Maryland. Oxford is also home to the oldest privately operated ferry still in use in the country and we’ll take it across the bay to St. Michaels. You’ll have lunch on your own here – we highly recommend the crab cakes! You can take the time to visit the Chesapeake Bay Maritime Museum or window shop along Main Street before cycling back to Easton. 32 or 44 miles, ±287' or ±461'

DAY 4: After a 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. 21 miles ±342'.