September Family Event: Annapolis Day 2026

  • September 19, 2026
  • 12:00 PM - 4:30 PM
  • Schooner Woodwind (80 Compromise St, Annapolis, MD 21401)
  • 87

Registration


Register


Brethren of Singleton Lodge, mark your calendars and reserve your tickets for our annual voyage aboard the historic Schooner Woodwind in beautiful Annapolis, Maryland.

The Worshipful Master cordially invites the Brethren of Singleton Lodge No. 7 and their families to join us for one of our most cherished summer traditions—a memorable afternoon of fellowship, sailing, and Chesapeake Bay adventure.

Year after year, Annapolis Day has become one of the Lodge's premier family events, bringing together Brothers, spouses, children, and friends for an unforgettable experience on the water. As we set sail from Annapolis Harbor, guests will enjoy breathtaking views, fresh bay breezes, and the unique opportunity to cruise aboard an authentic schooner under full sail.

Space aboard the Woodwind is limited to just 40 passengers, and this event routinely sells out. We encourage everyone to secure their reservations early.

Beverages will be available for purchase during the sail, and the Lodge is finalizing plans for a catered gathering following our return to shore. Additional details will be shared as they become available.

To reserve your spot, please complete your payment through CheddarUp. Reservations that remain unpaid may be released to accommodate Brothers and families on the waiting list.

Date: September 19

Time: 12pm (SHARP)

Invited: Lodge Members and their Families

Cost: $30/adult | $5/child

Purchase Tickets Here: CheddarUp Link 

Important: To secure your tickets, please complete payment at the following link: https://annapolis-harbor-cruise-2026.cheddarup.com/

We hope you will join us for an afternoon of fellowship, family fun, and a little maritime adventure as Singleton Lodge returns once again to the waters of the Chesapeake Bay.