Dewey Beach Fall and Winter Events 2026: Halloween Through the Crush Drop
Summer gets the crowds, but Dewey keeps the party going long after the umbrellas come down. A haunted graveyard on the beach, a tree lighting with Santa, and a giant Orange Crush counting down to midnight. Keep the beach sweatshirt handy.
Dates and details can change. Confirm with the venue or organizer before heading out.
October: Halloween at the beach
Dewey Beach Trick or Treating, town-wide
Friday, October 23, from 6:30 to 7:30 PM. It’s a one-hour window, so have the costumes on and the candy bags ready before you head out.
Haunted Bonfire & Haunted Graveyard, Dickinson Avenue
Friday, October 23 and Saturday, October 24. Yes, the graveyard is on the beach. Halloween with sand in your shoes is about as Dewey as it gets.
Insider Tip: Friday makes an easy one-night plan: trick-or-treat first, then head over to the bonfire. Check the Dewey Business Partnership’s events page for start times.
Sea Witch Festival, downtown Rehoboth Beach
October 23 to 25, just up the road. The costume parade comes down Rehoboth Avenue at 11 AM on Saturday, October 24. It’s free and it draws a big crowd, so give yourself extra time to park and get around.
November: films and the first twinkle lights
Rehoboth Beach International Film Festival, Cinema Art Theater, 17701 Dartmouth Drive, Lewes
November 1 to 8, now celebrating 28 years. A full week of independent and international film, a short drive up Route One.
The Vibe: Quiet beaches by day, movies by night. If you’ve never done an off-season weekend at the coast, this is a good excuse to try one.
Dewey Beach Tree Lighting, Fifer’s Market, Highway One
Saturday, November 28, at 5:30 PM, with Santa arriving at 6:15. It’s the Saturday after Thanksgiving, so bring the visiting relatives.
Insider Tip: Get there a little early if your kids want a spot up front when Santa shows up.
December: Santa crawls and the Crush Drop
Dewey Santa Crush Crawl, starting at Starboard Claw
Saturday, December 5, from noon to 9 PM. Pull out your best Santa outfit and make a day of it. Plan your ride home before the first round.
Dewey Crush Drop, Route One and New Orleans Avenue
Thursday, December 31, at 11:30 PM. A giant Orange Crush replica comes down at midnight to ring in 2027. Dewey’s answer to the Times Square ball drop, and a lot easier to get to.
New Year’s Eve at Bottle & Cork, 1807 Highway One
The Electric Dewey Carnival with Knappy’s LVLS EDM party kicks off at 9 PM on December 31. Check their website for tickets.
New Year’s Eve at the Rusty Rudder, 113 Dickinson Street
Prefer bands? The lineup includes Love Seed Mama Jump, Stealing Savanah, Gab Cinque, and Kono Nation. Check their website for tickets and times.
Don’t Miss: The Crush Drop and both NYE parties are a short walk apart, so you can catch the countdown and still make it back inside.
Before you go: off-season hours
Plenty of Dewey spots cut back their hours or close for the winter once summer wraps up. Check before you build a night around one.
Northbeach is closing for good after the 2026 season, after 27 years on the bay. According to Milford LIVE, Bent Palm, a new restaurant from Dewey Beach Country Club owner Greg Plummer, is expected to take over the space. If you want one more visit, check Northbeach’s social pages for their final days.
See you at the beach, sweatshirt and all.
Updated October 19, 2026