Cambridge to Taylors Island in Dorchester County, MD

Updated: August 23, 2012

Begin your journey at the intersection of Gay and Race Streets, in historic downtown Cambridge. Free parking is available along the streets and in nearby parking lots.

Ride down Race Street toward Washington Street, passing the Harriet Tubman Museum, shops, art galleries and restaurants. Come to a stop at Washington Street (.4) and turn right. Follow Washington Street/Route 343, which becomes Hudson Road/Route 343, until you reach a fork (2.8) where a store is located. Bear to the left and continue on Route 343.

Turn left on Town Point Road (3.9) and continue as it becomes Dailsville Road (5.8). Follow Dailsville Road and make a right on Church Creek Road/Route 16 (8.5), where the Stanley Institute, a 19th century, one-room, African American schoolhouse, is on your left.

On Route 16 you will pass a produce stand (10.5) on your right and enter the village of Church Creek (11.6), just before passing a restaurant (11.9) on your left. Next, pass Golden Hill Road/Route 335 (12.7) on your left, and then Old Trinity (13.7), a restored 18th century colonial church, on your right. Next, you will pass a store (14.4).

Route 16/Church Creek Road becomes Route 16/Taylors Island Road. Continue on Route 16, passing a bed and breakfast (16.1) on your left, as you ride through the villages of Woolford and Madison. As you approach the bridge over Parson’s Creek (19.9), note Stewart’s Canal to your left. The six-to-seven mile canal was dug by enslaved African Americans between 1810 and the 1830s. Harriet Tubman learned important survival skills when she and her father worked in the Stewart family timbering operations.

Before crossing the bridge onto Taylors Island, you will pass a restaurant and a store at a marina (21.7) on your right. After you enter Taylors Island (22), you will see another restaurant (22.6) on your right, and a bed and breakfast on the left. Now, turn around and retrace your route.

Ride Length: About 45 miles

This route and map provided courtesy of Dorchester County Tourism with their prior permission. You can visit them online at and download the brochure containing this map at

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