16th Annual Round Island Regatta – It’s a Family Fun Regatta for all ages in Portsmouth! Sat. August 15th.

Sail, Paddle or Row in the 16th Round Island Regatta!

Join the nonprofit Gundalow Company’s 16th annual Round Island Regatta at Peirce Island Boat Launch on Saturday August 15th 2026 between 1PM and 4PM! Our tradition continues with a prize awarded for best competitor costume! This years theme is 1776/Revolutionary War (no weapons please) and our awards ceremony will include snacks and desserts.

Registering in advance helps us prepare for the right number of guests and keep this event running each year. We’ve secured snacks and treats for after the race.

This is a very family friendly event – we’re aiming for prizes for all kids, and have free snow cones. Kids can also assemble and decorate their own Gundalow model for the “Great Little Gundalow Derby” from the dock.

Registration $30 for adults, $15 for children.

Please note that we will NOT be providing lunch this year.

Schedule
HIGH WATER AT 2:10PM

1:00PM-2:30PM
Registration Open (Peirce Island Boat Launch)

2:00PM
Sailboat Skippers Meeting
(Peirce Ramp, please have boats launched and rigged prior)
Class 1 Sailboat Start On The Water
Little Gundalow Derby (Peirce Island Dock)
Youth Paddle Skippers Meeting (Peirce Ramp)
Youth Paddlers Start

2:30PM
Paddle & Oar Skippers Meeting (Peirce Ramp)
First Wave: Lady Isle Start

Second Wave: Round Island Start
Kayakers, then Stand Up Paddleboards, then Rowers
Second Wave: Round Island Start
Kayakers, then Stand Up Paddleboards, then Rowers

3:15PM
Awards ceremony & Desserts (Four Tree Island)

Course
Courses will be described at the sail and paddle skipper’s meetings prior. Sailors will go between one and three times around Round Island and the marks set by the race committee. Rowers and paddlers will have the option of doing the standard twice around Round Island Course (1 mile) or the longer Lady Isle course (1.9 miles), also starting and finishing near the Peirce Island Ramp.

Class
Sail Class — all trailer-able sailboats
Lady Isle long course– optional for experienced rowers and paddlers
Youth Paddler Class (ages 13 and under)
Single Paddler (ages 14+, paddle and oar)
Multi-Paddlers (all paddle and oar craft with two or more people)

Stand up paddle boards are considered boats by the USCG and the State of NH. Accordingly, all persons using a SUP are required to carry a wearable life jacket onboard while paddling. The Marine Patrol also reminds boaters/paddlers that anyone 12 years of age and under must be wearing their life jacket at all times while aboard any type of boat/SUP.

“Round Island” Regatta Course
Starting near the South End Yacht Club, leave Round Island and both race marks (here labeled SE and NW) to PORT for two loops before heading to the finish.

3000 ft / ½ nautical mile each loop, total around 1 mile.

“Lady Isle” Regatta Course
Starting near the South End Yacht Club, leave Round Island to PORT, pass under the New Castle Ave Bridge, leave Lady Isle (AKA Belle Isle) to PORT, and return through the bridges by the shortest route.

Round Island Regatta 2026
Location: Peirce Island Boat Ramp, Portsmouth NH