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The 27th Annual Castine Classic Yacht Race is a 19.4-nautical-mile sailing race from Castine to Camden across Penobscot Bay, hosted by the Castine Yacht Club. Held since 1999, it attracts a fleet of classic and Spirit of Tradition yachts and is the first of three days of racing culminating with the Eggemoggin Reach Regatta.
Other public events whose dates overlap with this one.
Maine's Best Sailing Regattas: A Guide to the Midcoast Racing Season
Maine's midcoast is home to some of the best sailing regattas in the Northeast — from the Great Schooner Race to the Camden Classics Cup to the Eggemoggin Reach Regatta. Here's your guide to the racing calendar and what makes each event special.
Apr 7, 2026
Salem Haunted Happenings 2026: What's On, When, and How to Plan Your October
Salem spends all of October as Halloween's unofficial capital. Haunted Happenings 2026 runs October 1-31, anchored at Salem Common, with the Grand Parade on Friday, October 2. Here's how to plan a visit — and what you'll want to confirm with the organizers before you go.
Sep 4, 2026
Southington Apple Harvest Festival 2026: Free, Huge, and Two Weekends Long
One of New England's largest and longest-running fall festivals, free to get into, spread across two October weekends on the Southington Town Green.
Sep 4, 2026