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HIGHLIGHTS

A quick look about this trip!

DURATION

4 DAYS

COMFORT

STYLE

LANGUAGE

RATING

We’ll bike south along the meandering flat roads of the Eastern Shore to St. Paul’s Episcopal Church, a parish founded in 1693.
We’ll head north for our second bike ride toward the small town of Betterton.
Head out on our bikes for a short trip to the bay.
We’ll explore more of the quiet back roads of Kent County, cycling through forests and farmland to the African American Schoolhouse Museum.

ACTIVITIES ON THIS TRIP

Primary:	Road Cycling
Other:	Museums & Expositions, Parks & Nature Reserves, Historical Sites, Kayaking, Swimming, Wildlife, sightseeing, Urban Exploration

$1190USD

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TRIP MAP

See the locations you'll visit!

Maryland Eastern Shore - Northern

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.

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TRIP OVERVIEW
TRIP ITINERARY
NUTS & BOLTS

Meet: Chestertown, MD

Time: 2:30pm

Terrain: Flat terrain. Beginner to moderate cycling level.

Travel Arrangements: 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.

Day 1: Chestertown, MD

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: Betterton

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: Davis Creek and Long Cove Landing

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: Depart

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.

TRIP INCLUDES

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

TRIP DOES NOT INCLUDE

Rental Bike: $175

CANCELLATIONS: 20% cancellation fee applied if cancelled 60 days prior to departure. Cancellations within 60 days are 100% non-cancelable

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<center>
        <h1 style="margin: 0px; font-family: 'philosopher'; font-weight: bold; font-size: 22px; color: #604c3d;">Maryland Eastern Shore - Northern</h1>
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    <div style="margin-top: 5px; margin-bottom: 10px; font-family: 'Futura Bold', 'Gill Sans', Arial, 'Helvetica Neue', Helvetica, sans-serif; font-size: 15px; line-height: 20px; color: #928164;">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. </div>

<div style="margin-top: 10px;border-radius: 5px; 	
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                                    <div style="font-family: 'philosopher'; font-weight: bold; font-size: 10px; color: #907878; padding-top: 5px;">DURATION</div>
                                    <div style="font-family: 'alice'; font-size: 18px; color: #7a9ebf; padding-top: 10px;">4 <span style="font-size: 10px;">DAYS</span></div>
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                                    <div style="font-family: 'philosopher'; font-weight: bold; font-size: 10px; color: #907878; padding-top: 5px;">STYLE</div>
                                    <div style="padding-top: 5px;">
                                        <span style="display: inline-block;" class="sprite_icons icn_style_woman btnStyleClass" data-hover="<b>Women Only</b> – Whether it is exploring the archaeology of Peru or Greece, or hiking your way
                                      through the Italian Alps, pick your destination and interest of choice, and join like-minded women
                                      for an unforgettable adventure."></span>
                                    </div>
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                                    <div style="font-family: 'philosopher'; font-weight: bold; font-size: 10px; color: #907878; padding-top: 5px;">LANGUAGE</div>
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                                    <div style="font-family: 'philosopher'; font-weight: bold; font-size: 10px; color: #907878; padding-top: 5px;">RATING</div>
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                                        <span class="sprite_icons icn_star_selected" style="display: inline-block;"></span><span class="sprite_icons icn_star_selected" style="display: inline-block;"></span><span class="sprite_icons icn_star_selected" style="display: inline-block;"></span><span class="sprite_icons icn_star_selected" style="display: inline-block;"></span><span class="sprite_icons icn_star_selected" style="display: inline-block;"></span>
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                        <div style="font-family: 'sorts mill'; font-size: 13px; color: #544741; margin-top: 20px;" id="Div1">
                            <div><ul><li>We’ll bike south along the meandering flat roads of the Eastern Shore to St. Paul’s Episcopal Church, a parish founded in 1693.<li>We’ll head north for our second bike ride toward the small town of Betterton.<li>Head out on our bikes for a short trip to the bay.<li>We’ll explore more of the quiet back roads of Kent County, cycling through forests and farmland to the African American Schoolhouse Museum.</li></li></li></li></ul></div>
                        </div>
                    </div>
                    <div style="margin-top: 10px; padding: 10px;border-radius: 5px; 	
	-moz-border-radius: 5px; 
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	border: 1px solid #dddddd;
	background-image: linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -o-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -moz-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -webkit-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -ms-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);

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		linear,
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		color-stop(0.81, #FEFEFE)
	);
	background-color: #FEFEFE;">
                        <div style="font-family: 'philosopher'; font-weight: bold; font-size: 14px; color: #604c3d; text-align: center;">ACTIVITIES ON THIS TRIP</div>
                        <table cellpadding="5" style="margin-left: 5px; margin-right: 5px; margin-top: 5px;">
                            <tr>
                                <td><span style="color: #544741;">Primary:</span></td>
                                <td><a href="/search/for/Road%20Cycling/in/Anywhere%20in%20the%20World/any-travel-style">Road Cycling</a></td>
                            </tr>
                            
                            <tr>
                                <td><span style="color: #544741;">Other:</span></td>
                                <td><a href="/search/for/Museums%20%20Expositions/in/Anywhere%20in%20the%20World/any-travel-style">Museums & Expositions</a>, <a href="/search/for/Parks%20%20Nature%20Reserves/in/Anywhere%20in%20the%20World/any-travel-style">Parks & Nature Reserves</a>, <a href="/search/for/Historical%20Sites/in/Anywhere%20in%20the%20World/any-travel-style">Historical Sites</a>, <a href="/search/for/Kayaking/in/Anywhere%20in%20the%20World/any-travel-style">Kayaking</a>, <a href="/search/for/Swimming/in/Anywhere%20in%20the%20World/any-travel-style">Swimming</a>, <a href="/search/for/Wildlife/in/Anywhere%20in%20the%20World/any-travel-style">Wildlife</a>, <a href="/search/for/sightseeing/in/Anywhere%20in%20the%20World/any-travel-style">sightseeing</a>, <a href="/search/for/Urban%20Exploration/in/Anywhere%20in%20the%20World/any-travel-style">Urban Exploration</a></td>
                            </tr>
                            
                        </table>
                    </div>

<div style="border-radius: 5px; 	
	-moz-border-radius: 5px; 
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	background-image: -o-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -moz-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -webkit-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);
	background-image: -ms-linear-gradient(bottom, #F3F3F3 2%, #FEFEFE 81%);

background-image: -webkit-gradient(
		linear,
		left bottom,
		left top,
		color-stop(0.2, #F3F3F3),
		color-stop(0.81, #FEFEFE)
	);
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	-moz-border-radius: 5px; 
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	margin-top: 15px;">
                                    <div style="margin-top: 5px; margin-bottom: 10px; font-family: 'sorts mill'; font-size: 16px; font-weight: bold; color: #604C3D;">
                                        Day 1: Chestertown, MD 
                                    </div>
                                    <div style="margin-top: 5px; font-family: 'Futura Bold', 'Gill Sans', Arial, 'Helvetica Neue', Helvetica, sans-serif; font-size: 13px; color: #544741; line-height: 20px;">
                                        <div>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.</div><div><br></div><div>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.</div><div><br></div><div>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.</div>
                                    </div>
                                    
                                    </div>
                            
                                <div style="margin: 0px 0px 10px 0px; border-radius: 5px; 	
	-moz-border-radius: 5px; 
	-webkit-border-radius: 5px; 
	border: 1px solid #dddddd;
	background-color: White;
	padding: 10px;
	margin-left: 10px;
	margin-right: 10px;
	margin-top: 15px;">
                                    <div style="margin-top: 5px; margin-bottom: 10px; font-family: 'sorts mill'; font-size: 16px; font-weight: bold; color: #604C3D;">
                                        Day 2: Betterton
                                    </div>
                                    <div style="margin-top: 5px; font-family: 'Futura Bold', 'Gill Sans', Arial, 'Helvetica Neue', Helvetica, sans-serif; font-size: 13px; color: #544741; line-height: 20px;">
                                        <div>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.</div><div><br></div><div>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.</div><div><br></div><div>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.</div><div><br></div><div>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.</div>
                                    </div>
                                    
                                    </div>
                            
                                <div style="margin: 0px 0px 10px 0px; border-radius: 5px; 	
	-moz-border-radius: 5px; 
	-webkit-border-radius: 5px; 
	border: 1px solid #dddddd;
	background-color: White;
	padding: 10px;
	margin-left: 10px;
	margin-right: 10px;
	margin-top: 15px;">
                                    <div style="margin-top: 5px; margin-bottom: 10px; font-family: 'sorts mill'; font-size: 16px; font-weight: bold; color: #604C3D;">
                                        Day 3: Davis Creek and Long Cove Landing 
                                    </div>
                                    <div style="margin-top: 5px; font-family: 'Futura Bold', 'Gill Sans', Arial, 'Helvetica Neue', Helvetica, sans-serif; font-size: 13px; color: #544741; line-height: 20px;">
                                        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.<div><br></div><div>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.</div>
                                    </div>
                                    
                                    </div>
                            
                                <div style="margin: 0px 0px 10px 0px; border-radius: 5px; 	
	-moz-border-radius: 5px; 
	-webkit-border-radius: 5px; 
	border: 1px solid #dddddd;
	background-color: White;
	padding: 10px;
	margin-left: 10px;
	margin-right: 10px;
	margin-top: 15px;">
                                    <div style="margin-top: 5px; margin-bottom: 10px; font-family: 'sorts mill'; font-size: 16px; font-weight: bold; color: #604C3D;">
                                        Day 4: Depart
                                    </div>
                                    <div style="margin-top: 5px; font-family: 'Futura Bold', 'Gill Sans', Arial, 'Helvetica Neue', Helvetica, sans-serif; font-size: 13px; color: #544741; line-height: 20px;">
                                        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.<div><br></div><div>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.</div>
                                    </div>
                                    
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                <img style="width: 660px; padding: 2px; border: 1px solid #ccc; margin: 10px;" src="https://d35b54kuuvhi57.cloudfront.net/946e1cd8-4c5c-4a80-9338-c58529ace1b7.jpg" />
    
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                <img style="width: 660px; padding: 2px; border: 1px solid #ccc; margin: 10px;" src="https://d35b54kuuvhi57.cloudfront.net/37fdc312-4c67-4d93-8eeb-fe8192a21e26.jpg" />
    
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                <img style="width: 660px; padding: 2px; border: 1px solid #ccc; margin: 10px;" src="https://d35b54kuuvhi57.cloudfront.net/d95cacca-395d-416e-ad65-f7a052442ac4.jpg" />
    
                <img style="width: 660px; padding: 2px; border: 1px solid #ccc; margin: 10px;" src="https://d35b54kuuvhi57.cloudfront.net/3b0b47f1-15b2-4145-be48-b2a0e42c6fd0.jpg" />
    
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