Cypress Island

Beach Camp and Trail Running Extravaganza 

Our Sucia weekend was such a success in 2019, that we’re super excited to add a second Beach Camp and Trail Run destination: Cypress Island. Cypress is a bigger island, which means more trails and the potential for more miles or simply an excuse to get away from it all for another weekend.


  • Friday through Sunday, July 24-26, 2020


Cypress Island is part of the larger San Juan archipelago. Largely off the radar, this uninhabited island is heavily forested and designated as a conservation reserve. The island boast over 20 miles of trails that lead to high vistas, remote beaches, and forgotten lakes. The perfect recipe for a weekend of island exploration.

Course Overview

Friday, Day 1: Boat Taxi to Cypress

We’ll meet at 4:00pm for a 4:45 sail from Anacortes, WA. It’s a short sail to Pelican beach where we’ll be based out of for the weekend. We’ll have appetizers, drinks, and dinners on the beach and trek up to Eagle’s Nest lookout for the sunset.

Saturday, Day 2: 5-20 Miles of Trail Running + Paddle Sports

Cypress is a mid-sized island with a network of 20+ miles of trails that loop in and around the island. We’ll organize some formal groups to explore, but runners will also be free to roam wild throughout the island.

Sunday, Day 3: Morning Run/Paddle, Boat Taxi Home

After breakfast, morning runs and/or relaxing on the beach, we’ll eat lunch and break camp before catching our boat taxi around 1pm and arrive Anacortes by 2pm. 


For topographical route information and a view of the islands trails, visit our Caltopo Map of Cypress Island. 

Trip Accommodations

Our Cypress basecamp will be staged out of the Pelican Beach group campground and group shelter. Aspire will provide a lively camp amenities for a remote but comfortable “glamp” style experience.


Cypress is not services by any public ferry service. Private boats are the only way to access the island.  Aspire has chartered a water taxi that will transport runners and equipment between Anacortes and Cypress Island.

Course Info Packet

For details about the trails, itinerary information, packing and gear lists, menu and dietary information, safety protocols, and trip policies, we’ve prepared a Cypress Island Course Info Packet. Share your email with us and we’ll send send you a link to the info.


Early Bird Registration: $350. Ends January 15th, 2019

Regular Registration: $400. Ends March 31st, 2020

Late Registration: $450. Closes July 19th, 2020

*Payment plans are available for every trip. Email us to set one up


Trip Insurance

Every year we have at least one runner who, due to injury, illness, or personal/familial circumstances, cannot participate in his or her registered trip. While registrations can be transferred, Aspire does not issue refunds. See our FAQ’s. We strongly encourage each runner to purchase 3rd party trip insurance that will reimburse the cost of registration in the event that he or she is unable to participate in the event.