Starting at $25 l 2 Hours l Ages 9+
Celebrate autumn on the Chesapeake Bay with the Halloween Parade paddle in Deale, Maryland. Enjoy two thrilling hours on the water with rental gear or your own board, suitable for paddlers aged nine and up.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
2 hours
Fitness Level
Suitable for people in average physical condition with basic paddling stamina, including beginners aged 9+.
Wildlife
History
Deale has a long-standing Chesapeake Bay fishing tradition, dating back to early colonial times when it served as a vital maritime community.
Conservation
The event emphasizes 'leave no trace' principles to protect the waterways and delicate bay ecosystems of Maryland.
Chesapeake Paddle Sports
Starting at $25 l 2 Hours l Ages 9+
Chesapeake Paddle Sports is a Deale, Maryland outfitter focused on accessible paddling experiences around the Chesapeake Bay and nearby creeks. The operation offers kayak rental, paddle board rental, double kayak rental, pedal boat rental, memberships, guided Sunrise SUP and Full Moon Paddle events, SUP 101 instruction, a Kids Summer SUP Camp, and social outings like SUNday FUNday.
Rentals and programs operate on Rockhold Creek, Tracey’s Creek, and Herring Bay, with programming designed to highlight local wildlife and shoreline history while reinforcing safe on-water skills. SUP 101 is taught by certified coaches and includes a complimentary 30-minute self-guided paddle after the lesson. The Kids SUP Camp runs four days for ages 8–14 and combines paddling skills, games, and Chesapeake Bay exploration.
Age and occupancy guidelines are stated for each offering: kayak and paddle board rentals are available to adventurers aged nine and up, and pedal boats accommodate up to two adults and one child. Special events include a guided Sunrise SUP (RSVP by 6 PM the night before) and a 90-minute Full Moon Paddle. Membership options cover SUP Yoga, fitness classes, and guided tours.
Booking and operations are based in Deale, Maryland, with activities staged on the listed creeks and Herring Bay. Chesapeake Paddle Sports emphasizes family-friendly options, certified instruction, and clearly stated age and occupancy guidelines for renters, campers, and class participants. Advance reservations help secure preferred dates and equipment today.
Location
Deale, Maryland
Activities launch from Deale on Herring Bay
Tours Offered
11
Rentals, classes, camps, and guided paddles
Kids Camp Ages
8–14
Four-day summer SUP camp for youth
Pedal Boat
2 adults + 1 child
Family capacity for pedal boat rentals
Book rentals, lessons, camps, or guided paddles on Rockhold Creek and Herring Bay — check age limits and RSVP details to secure a spot.
Check Weather Closely
Fall weather can be unpredictable on the Chesapeake—dress in layers and bring wind protection.
Use a Leash
For safety, always attach your paddleboard or kayak leash to prevent losing your board in choppy water.
Arrive Early
Arriving 15 minutes before start ensures time for gear fitting and safety briefing.
Hydrate and Snack
Bring water and a light snack to stay energized during the two-hour paddle.
Waterproof layered clothing
To stay warm and dry in the cool autumn breeze and potential splashes.
fall
Paddle Board or Kayak with leash
Safety leash keeps your board nearby if you fall in.
Water bottle
Hydration is important to maintain energy and focus on the water.
Sun protection (hat, sunglasses, sunscreen)
Even in fall, UV exposure on the water is strong and requires protection.
fall