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Itinerary:

Cannon Street: Revisiting the Customs of the Colonies

For those looking to steep themselves in plenty of local history, there’s no better place than Chestertown and the landing at Cannon Street. Chestertown was founded in 1706 and established as one of six Royal Ports of Entry. Ships entering the Chesapeake Bay had to come through one of these ports and pay taxes on things to be sold there, most likely at the building known as the Custom House. This building is located on the other side of the Riverfront Garden, at the foot of High Street. From the water, this means paddling toward the Chester River bridge.

The floating dock at the end of Cannon Street, meanwhile, puts paddlers on the water just in front of this historic community on the Chester River. Historic brick mansions from the 18th century line the waterfront at Water Street, providing stunning views of one of the best-preserved colonial seaports in the United States. 

Image Credit: Chris Cerino / Sultana Education Foundation

Things to Know

This site is a great place from which to explore Radcliffe Creek. The entrance is located about half a mile downriver from the dock, and features  scenery like freshwater marshes, forested shorelines, and unique views of the church spires rising above Chestertown.

Heading upriver it is just 2.5 miles to the mouth of Morgan Creek, though the Chester River is exposed to wind and should be paddled only on calm days. From this landing, it is 8.5 miles to Crumpton.

Navigational Hazards

This put-in site is located on the open waters of the Chester River; be aware of boat traffic, especially during warm weather months. Also pay attention to the wind; beginners should avoid paddling this location if there is a strong southerly wind.

Water Safety

Remember: safe use of rivers and any designated trails, at any time, is your responsibility! Water trail maps are for informational and interpretive purposes only and are not meant for navigational purposes, nor do they take into account level of skills or ability required to navigate rivers. The National Park Service, Chesapeake Conservancy and/or the individual trail associations assume no responsibility or liability for any injury or loss resulting directly or indirectly from the use of water trails, maps or other printed or web-based materials. Learn more about water safety.

Marine Forecast

We STRONGLY suggested that you review the marine forecast ahead of heading out for a paddling trip. To review the forecast for this paddle trip, visit:

Emergency Information

Launch site address:
End of Cannon Street
Chestertown, MD 21620

Nearest hospitals:
UM Shore Medical Center at Chestertown
100 Brown St
Chestertown, MD 21620
(410) 778-3300

Chester River Hospital Center
6602 Church Hill Rd #300
Chestertown, MD 21620
(410) 778-3300

Parking & Shuttles

Paved, marked spaces for 10+ vehicles

Restrooms

No, portable toilet two blocks south at Wilmer Park

Equipment

  • ALWAYS wear a properly secured personal flotation device (PFD) when participating in paddlesport activities. Make sure that your PFD has a readily accessible safety whistle.
  • Bring a paddle float and water pump for self rescue.
  • A spray skirt is recommended for cold/foul weather.
  • Wear appropriate protective clothing that shields you from the sun (sunglasses, sunblock, hat, and a long-sleeved shirt that can get wet) and is safe to swim in. Water shoes with closed toes will protect you from abrasive hazards at launch areas that can cut your feet.
  • Bring water in bottles than can be secured to your craft. Bring more water than you think you’ll need and drink regularly throughout your journey.
     

Outfitters

Camping & Amenities

This launch site has a floating dock from which to launch kayaks or canoes.

There are no camping amenities on site.

Trail History

Founded in 1706 as one of six original Royal Ports of Entry, Chestertown is one of the best-preserved colonial seaports in the United States. In the latter half of the 18th century, grain shortages in Europe allowed Chestertown’s merchants to ship local foodstuffs abroad for tremendous profits. The grandiose brick mansions they constructed still line the river today. In the 21st century, Chestertown’s scenic waterfront, brick-lined streets, and plentiful shops make it a popular tourist destination. The schooner Sultana is a full-scale reproduction of a 1768 topsail schooner used historically to enforce British taxes in colonial waters in the years preceding the American Revolution. Constructed by professional shipwrights and volunteers in Chestertown, Maryland, the modern Sultana provides educational programs to 5,000 students each year focusing on colonial history and environmental science. 

Weather

Main image: Chris Cerino / Sultana Education Foundation