Annually, Sailing Through The Winter Solstice begins in November, when a number of boats, transformed through the creative minds of many Frederick friends, set sail on the Creek. Our fleet has grown from one boat the first year to 26 sailing boats and 1 land-locked boats in the 2024-25 season. The boats are anchored in Carroll Creek, between Market Street and Carroll Street.

The fleet includes gaff-rigged ketches, yawls, three-masted schooners, and pirate ships, moored with their sail outlines, rigging and decks lit up from dusk till dawn. If you can’t imagine it make sure to come by and take a look at the amazing flotilla!

It’s not just fun, it’s for a purpose. By voting for your favorite boat, organizations are raising awareness and money for amazing causes local to the Frederick community. All proceeds raised during STTWS go to each boat’s designated charity and Color On The Creek. The event runs from mid-November through the 2nd Saturday in March.

In addition to voting for your favorite boat ($5 per vote), many organizations are raising awareness and money for amazing causes. Visit the 2025-26 fundraising site to learn more about the 28 boats & 1 land shark in this years fleet.   All proceeds raised during STTWS go to each boat’s designated charity and Color On The Creek. The event runs from mid-November through the 2nd Saturday in March.