The East End of Long Island is quiet in winter, which is exactly what makes its holiday traditions special. Seaside villages light up their harbors and lighthouses, Main Streets glow, and the crowds of summer are replaced by locals gathering around trees with hot chocolate. If you want a cozy Christmas weekend away from the city, the Hamptons and North Fork are hard to beat.
Quick Facts
| Montauk Lighthouse Lighting | Saturday, November 28, 2026 |
|---|---|
| Sag Harbor “Light Up the Harbor” | Friday, December 4, 2026 |
| Magic of Montauk Holiday Fair | Saturday, December 12, 2026 |
| Getting there | LIRR Montauk Branch; Hampton Jitney from Manhattan; about 2.5–3 hours by car |
Montauk: Lighting of the Lighthouse
The Montauk Chamber of Commerce’s annual Lighting of the Lighthouse takes place on Saturday, November 28, 2026, the weekend after Thanksgiving. Montauk Point Lighthouse, New York State’s oldest, is outlined in holiday lights, with live music and hot chocolate. In past years the lights have switched on around 5:15 p.m.
Sag Harbor: Light Up the Harbor
On Friday, December 4, 2026, Sag Harbor lights its Long Wharf lighthouse and tree with holiday music at the waterfront. Main Street’s shops stay open late, and the American Hotel bar is the classic warm-up stop.
Magic of Montauk Holiday Fair
The Montauk Chamber and Visit Montauk’s 5th annual Magic of Montauk holiday fair is on Saturday, December 12, 2026, with local vendors and holiday activities.
North Fork Traditions
- Greenport Parade of Lights: an early-December evening parade on Main and Front Streets to Mitchell Park, with Mr. and Mrs. Claus on a fire truck and a tree lighting at the end.
- Southold Historical Museum Candlelight Tour & Tree Lighting: free holiday open house in decorated historic houses, usually the weekend after Thanksgiving.
- Orient Beach State Park tree lighting: Santa photos, cocoa and cookies in early December.
- The Big Duck lighting (Flanders): Long Island’s famous roadside duck gets its holiday lights in early December, with Santa and carolers.
Where to Stay and Eat
Many East End inns offer quieter, cheaper rates in December. Greenport and Sag Harbor are walkable bases with year-round restaurants. North Fork wineries often host holiday tastings and tree lightings too.
Frequently Asked Questions
When is the Montauk Lighthouse lighting 2026?
Saturday, November 28, 2026.
When is Sag Harbor Light Up the Harbor 2026?
Friday, December 4, 2026.
What holiday events are in the Hamptons?
Highlights include the Montauk Lighthouse lighting, Sag Harbor’s Light Up the Harbor, the Magic of Montauk holiday fair and village tree lightings across the East End.
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