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Paddling the Farmlands of Deep Landing

Once a busy commercial shipping site, Deep Landing is now very popular as a paddling location in the spring and summer. In the 18th century, many public landings on the Chester River operated as commercial ports for shipping agricultural products from plentiful eastern shore farmlands to ports in the Chesapeake and beyond. Grain was especially important to the economy of Queen Anne’s and Kent Counties. Bolstered by technological improvements in farm machinery and transportation, farming took off on the eastern shore until an agricultural depression began in 1890. 

You can paddle through modern-day farmlands by heading about 1.5 miles upstream from the launch site to Crumpton, where the shoreline eventually becomes forested, or by paddling toward Chestertown, which lies 7 miles downstream. This stretch of the Chester often features strong currents. Make sure to plan your trip and note the tides.

Things to Know

It is a 1.5 mile journey upsteram to the town of Crumpton, passing farmland along the way. Beyond the Crumpton Bridge, the waters narrow all the way to Millington at the head of the river.

Downstream, the scenery is mostly large farms for several miles. Chestertown is 7 miles downstream from the landing.

Navigational Hazards

This ramp is situated on an area of the Chester with strong currents, especially immediately off the landing itself. Be aware of which way the tide is flowing. Also be aware that this ramp is quite popular and gets busy during summer months.

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 Deep Landing Road
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 parking for up to 20 vehicles


Seasonal portable toilets (April-November)


  • 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.


Camping & Amenities

This site has a concrete ramp for launching small or motorized vessels.

There are no camping amenities on site.

Trail History

Before the Civil War, the farmlands of Kent and Queen Anne’s Counties began to be known for their bounty of corn, wheat, and fruit. The introduction of the railroads to these areas opened them up for shipping to other counties in Maryland and beyond, which bolstered the economy of these places greatly. This growth was also accelerated by technological improvements in farm machinery. Shipbuilders in the 18th century enhanced trade by building small boats for local transportation, in addition to larger-masted vessels for trade internationally. Eventually the great steamboats of the early 20th century allowed for increased trade and tourism, bringing products and people to and from the eastern shore. Though the eastern shore is largely characterized by wide open spaces and vast farmlands, advancements and innovations in transportation have allowed for the spread of products, a boost to the economy, and the movement of people to these less-habited shores. 


Main image: Spielmann