Greyhounds Reach the Beach
Hundreds of greyhound owners and their dogs gather over Columbus Day weekend for vendors, seminars and a boardwalk parade.
Events
Festivals, parades, markets and food events from Milton to Fenwick Island, from now through spring.
Coming up
October
Thu8Oct
Scarecrow Trail & Show
Businesses around Rehoboth and Dewey display decorated scarecrows all month for visitors to find and vote on.
Tania Dibbs Solo Exhibition
A solo show of work by the Colorado painter at Peninsula Gallery.
Crooktoberfest
Crooked Hammock's month-long Oktoberfest-style party with German food, festival beers, live entertainment and stein-holding contests.
Fri9Oct
The Rocky Horror Show
Clear Space's Halloween-season production of the cult rock musical, with late-night audience-participation shows on Saturdays.
Sat10Oct
Boardwalk Buddy Walk
Walk on the Boardwalk starting at the Bandstand to raise awareness for people with Down syndrome.
Punkin Ale Fest Free (puppy yoga $25)
Free, family- and dog-friendly fall festival at Dogfish Head's Milton brewery with Punkin Ale, vendors, food trucks, live music and pumpkin painting.
OktoBOARDFest at The Starboard
The Starboard's Oktoberfest party with live music from PolkADelphia (1pm), Scotty Pip & Friends (4:30pm) and The Amish Outlaws (9pm).
Haunting History Tour $35
A night-time paranormal investigation of Lewes legends on the Historic Lewes campus.
Sun11Oct
The New Adventures of Aunt Mary Pat $25.03-$32.65
Comedy show at the Milton Theatre for ages 18 and up. Doors open at 6:30pm.
Thu15Oct
Rehoboth Beach Jazz Festival Varies by show (free to $179)
The 37th annual festival brings national smooth-jazz and R&B headliners to stages in Rehoboth, Lewes and Dewey over four days.
True Blue Jazz Festival $35-$85 per show
Straight-ahead jazz festival with ticketed shows at the Boardwalk Plaza Hotel and a big-band marathon at the Rehoboth Beach Fire House.
Miss Richfield 1981: You Can't Have Ice Cream When You're Dead! $39.86-$49.13
Comedy show at the Milton Theatre for ages 18 and up. Doors open at 6:30pm.
Sat17Oct
Historic Lewes Harvest Festival
Trade demonstrations, crafts and 18th-century entertainment showing life in Lewes in 1776.
Selbyville Trunk or Treat
The town's 6th annual trunk or treat in the fire company parking lot.
Zombie Fest 2026: Undead Disco $5 online / $10 at gate; kids 12 and under free
The Milton Theatre's Halloween festival with costume contests, live music, zombie makeup, vendors, food trucks, a kids' area and fireworks.
Southern Delaware Therapeutic Riding Barn Dance
The 8th annual barn dance fundraiser for the therapeutic riding center.
Fri23Oct
Dewey Haunted Bonfire & Graveyard
Dewey Beach's Halloween bonfire and graveyard walk, held the same weekend as Sea Witch and the Dewey trick-or-treat.
Sea Witch Festival Most events free
Rehoboth's big Halloween weekend, with a costume parade down Rehoboth Avenue on Saturday, a dog costume parade, live music and family activities.
Boos and Brews Halloween Celebration Ticketed, 21+
A costumed Halloween night with a live band, food trucks and spooky storytelling.
Children's Fantasy Trail $7 per person
Trick-or-treat along a trail with storybook characters and live entertainment. Sunday ends at 7:30pm.
Thu29Oct
Daou Vineyards Wine Dinner $114 per person, gratuity included
A five-course fall dinner paired with Daou Vineyards wines, guided by Lisa Kurts.
Fri30Oct
Lightship Overfalls Haunted Ship
The historic lightship turns into a haunted ship for Halloween.
Halloween Costume Contest
Costume contest with a trip to the islands for best overall, plus $100 and $50 gift cards for scariest and most creative. 21 and over.
Sat31Oct
All Hallows Eve at Historic Lewes
A classic small-town Halloween for families, with mystery and folklore on the Historic Lewes campus.
November
Sun1Nov
Rehoboth Beach International Film Festival Passes and single tickets; special events $60-$100
The Rehoboth Beach Film Society's 28th annual festival, a week of independent and international films, filmmaker Q&As and special events.
Wed4Nov
Chef Cooking Demo Free; table reservation required
Watch the chefs cook a featured dish while you order from the menu, with complimentary bites. Cocktail hour starts at 5pm; reserve a table by email (45 guests max).
Sat7Nov
Holiday Craft Fair & Soup Sale
Handmade crafts and homemade soup at the senior center's holiday fair.
Rehoboth Art League Holiday Fair $5 adults; under 12 free
The 42nd annual fine craft show fills the Art League's historic campus with artisans selling jewelry, glass, ceramics and fiber art.
Analog-A-Go-Go Ticketed
Dogfish Head's festival of craft beer and analog music, with vinyl DJ sets, live music and a marketplace of record stores and music vendors.
Haunting History Tour $35
A night-time paranormal investigation of Lewes legends on the Historic Lewes campus.
Sun8Nov
Holiday Market at Southern Delaware Therapeutic Riding
Over 60 vendors in the indoor arena, with a craft show, farmers market and food trucks.
Wed11Nov
Veterans Open House at Fort Miles
A Veterans Day open house and Dress for Defense Day at the Fort Miles Museum.
Fri13Nov
13: The Musical
Clear Space Theatre stages the Jason Robert Brown musical about turning 13.
Fires of the Revolution
An evening in Lewes on the eve of the Revolution, with a bonfire, tavern drinks and a recreated effigy-burning protest.
Sat14Nov
Holiday Boutique and Book Sale
The Friends of Cape Henlopen State Park holiday gift boutique and used-book sale at the park's Officers Club.
Schellville Enchanted Winter Celebration Free (some special events ticketed)
Free holiday village behind the Tanger Outlets with decorated mini-houses, a snow zone, sledding hill, live entertainment and Santa visits.
Haunting History Tour $35
A night-time paranormal investigation of Lewes legends on the Historic Lewes campus.
Fri27Nov
A Christmas Story (musical)
Clear Space's holiday musical version of the classic movie about Ralphie's quest for a Red Ryder BB gun.
Christmas Tree Lighting & Holiday Sing-Along
The city lights its community tree at the Bandstand after a holiday sing-along on the Friday after Thanksgiving.
Sat28Nov
Dewey Beach Tree Lighting
Dewey Beach lights its holiday tree the Saturday after Thanksgiving, with a second tree lighting on the Baywalk Dec. 5.
Small Jewels Exhibition
The gallery's 22nd annual show of small, affordable artworks for holiday gifts.
Old Town Market & Tree Lighting
Ocean View's eighth annual holiday market and tree lighting in John West Park.
December
Wed2Dec
Chef Cooking Demo Free; table reservation required
Watch the chefs cook a featured dish while you order from the menu, with complimentary bites. Cocktail hour starts at 5pm; reserve a table by email (45 guests max).
Thu3Dec
Lewes Hospitality Night
Evening holiday shopping with music downtown, plus extended hours and seasonal treats at the decorated Zwaanendael Museum.
Fri4Dec
Historic Lewes Holiday Market
Vetted artisans, outdoor fires and the Sussex Tavern, plus a greens sale at the barn on Saturday.
Selbyville Christmas Parade
The 65th annual hometown parade with floats, marching bands, fire trucks, antique cars and Santa.
Sat5Dec
Dewey Santa Crush Crawl
Holiday bar crawl through Dewey Beach's bars and restaurants.
Holiday Happenings in Bethany
Bethany Beach's holiday festival with trolley and beach-tractor rides, photos with Santa and the tree lighting at the bandstand plaza.
Rehoboth Seashore Marathon & Half Marathon $155 half / $175 full
Boston-qualifying marathon and half marathon on a flat course through Rehoboth and Cape Henlopen State Park.
Historic Lewes Holiday House Tour Ticketed
A tour of private Lewes homes decorated for the season.
Lewes Christmas Parade
Lewes's old-fashioned Christmas parade of floats and lights, followed by the tree lighting and candlelight caroling in Zwaanendael Park.
Mon7Dec
Rehoboth Beach Hometown Christmas Parade
The Rehoboth Beach Volunteer Fire Company's evening Christmas parade down Rehoboth Avenue.
Fri11Dec
Friends of Lewes Library Holiday Book Sale
Holiday book sale: Friday Dec 11, 3-5pm and Saturday Dec 12, 10am-2pm.
Sat12Dec
Rehoboth Art League Holiday Open House
Fine art, crafts and gifts at the 17th annual open house on the Art League campus.
Haunting History Tour $35
A night-time paranormal investigation of Lewes legends on the Historic Lewes campus.
Sat19Dec
Haunting History Tour $35
A night-time paranormal investigation of Lewes legends on the Historic Lewes campus.
Thu31Dec
Dewey Crush Drop (New Year's Eve)
The Dewey Business Partnership lowers a giant Orange Crush from a fire truck at midnight, oceanside at Route 1 and New Orleans Street. Free.
Family Anchor Drop
An early New Year's Eve anchor drop for families at the lightship.
New Year's Eve Anchor Drop
Ring in the new year as an anchor drops from the Lightship Overfalls at midnight.
January
Fri1Jan
First Day Hike at Cape Henlopen Free (park entry fees may apply)
A free guided New Year's Day hike around the Point at Cape Henlopen State Park.
Wed6Jan
Chef Cooking Demo Free; table reservation required
Watch the chefs cook a featured dish while you order from the menu, with complimentary bites. Cocktail hour starts at 5pm; reserve a table by email (45 guests max).
Fri29Jan
Fire & Ice Festival Free (some events ticketed)
The Quiet Resorts' 10th annual winter festival with 100+ ice sculptures, bonfires, live music, food trucks, kids' activities and a tasting tour.
Sat30Jan
Fire & Ice Chili Cook-Off Ticketed
A ticketed chili tasting and competition during the Fire & Ice Festival weekend.
February
Wed3Feb
Chef Cooking Demo Free; table reservation required
Watch the chefs cook a featured dish while you order from the menu, with complimentary bites. Cocktail hour starts at 5pm; reserve a table by email (45 guests max).
Regular happenings
Historic Lewes Farmers Market - Fall Market
The Historic Lewes Farmers Market moves to Saturday mornings at Lewes Elementary for its fall season of local produce, meat, baked goods and crafts.
Historic Lewes First Friday Community Night
Live music, colonial-style drinks, a coffee house and children's games at the Sussex Tavern, the first Friday of each month.
Historic Lewes Movie Night $5
Classic films in the museum theatre on the second Monday of each month, with refreshments available from the Sussex Tavern.
Mysteries of History Walking Tour
A walking tour of the darker and more unusual side of Lewes history. Also runs Thursdays Oct 1, 15 and 29.