Anyone who still thinks the Delaware beaches shut down after Labor Day has clearly never been here in October.
October is one of our favorite months in Rehoboth Beach.
The humidity drops. The boardwalk becomes a great place to actually walk. Dogs return to the beach. Restaurants are easier to enjoy.
And almost every weekend, something is happening. In fact, some October weekends are as busy as summer – just for entirely different reasons.
Here is the full rundown of October events in Rehoboth Beach for 2026, plus everything worth the short drive to Dewey Beach and Lewes.
October Events in Rehoboth Beach 2026 at a Glance
- October 2–4 – Fall Sidewalk Sale (Rehoboth Beach and Dewey Beach)
- October 3 – Dewey Goes Pink 5K and fundraiser (Dewey Beach)
- October 3 – Boast the Coast Maritime Festival (Lewes)
- October 8–11 – Greyhounds Reach the Beach (Rehoboth and Dewey)
- October 14–18 – True Blue Jazz (Rehoboth and Lewes)
- October 15–18 – Rehoboth Beach Jazz Festival (Rehoboth, Lewes and Dewey)
- October 18 – CAMP Rehoboth Block Party (Baltimore Avenue)
- October 23–25 – Sea Witch Festival (Rehoboth Beach and Dewey Beach)
Arriving before the leaves turn? Our September events guide covers Polkamotion, the Delaware Seafood Festival and Dewey’s Golden Jubilee.
Fall Sidewalk Sale | October 2–4
October starts with the Fall Sidewalk Sale, when stores throughout the Rehoboth Beach-Dewey Beach area move the shopping outside for a weekend of deals and end-of-season finds.
See Fall Sidewalk Sale details
For us, this is an easy weekend. Shop for a bit, eat somewhere downtown, walk the boardwalk, repeat only as necessary.
Dewey Goes Pink | October 3
Saturday belongs to Dewey.
Dewey Goes Pink returns October 3 with its annual 5K and fundraiser supporting the fight against breast cancer. The run moves through Dewey and portions of Rehoboth and has become one of the area’s major fall gatherings.
See the City of Rehoboth’s Dewey Goes Pink event information
Meanwhile, just north of Rehoboth, Lewes hosts another distinctly coastal event.
Boast the Coast | October 3
Boast the Coast Maritime Festival celebrates Lewes’ nautical history with free activities at 1812 Memorial Park overlooking the Lewes-Rehoboth Canal. The 2026 event runs from 11 a.m. to 2 p.m. and includes entertainment, family activities and free canal boat rides.
See 2026 Boast the Coast information
That gives you a pretty good Saturday: Dewey in the morning, Lewes in the afternoon and Rehoboth for dinner.
Greyhounds Reach the Beach | October 8–11
This is a big one for dog people.
Greyhounds Reach the Beach celebrates its 32nd year October 8–11, bringing Greyhounds, other sighthounds and their humans to Rehoboth and Dewey for four days of events.
Activities include speakers and vendors at the Convention Center, beach activities, walking tours, a bonfire and the Sunday Greyhound parade.
See the Greyhounds Reach the Beach schedule
Here’s the local tip that matters: under Rehoboth’s new 2026 rules, leashed dogs are permitted on the beach and boardwalk from September 16 through May 14 when lifeguards are not on duty.
So October really is dog season here. If you are building the whole trip around your dog, we keep a longer list of dog-friendly fall activities in Rehoboth Beach.
And yes, Canalside is genuinely dog-friendly – not simply a hotel that tolerates dogs.
Learn about staying at Canalside with your dog
Rehoboth Beach Jazz Festival | October 15–18
Then Rehoboth changes gears completely.
The Rehoboth Beach Jazz Festival returns October 15–18 with performances spread across Rehoboth, Lewes and Dewey, including the Rehoboth Beach Convention Center, Cape Henlopen Performing Arts Theater and Rusty Rudder.
See the official Rehoboth Beach Jazz Festival schedule and tickets
At the same time, True Blue Jazz presents its own festival programming in downtown Rehoboth and historic Lewes October 14–18.
Translation: if you like live jazz, this is your weekend.
CAMP Rehoboth Block Party | October 18
Sunday adds another reason to stay through the end of the weekend.
The CAMP Rehoboth Block Party takes over Baltimore Avenue on October 18 from 11 a.m. to 4 p.m.
Learn more about the CAMP Rehoboth Block Party
It’s very Rehoboth: local, lively and community-centered.
Sea Witch Festival | October 23–25
And then there’s Sea Witch.
If you’ve never been, it is difficult to adequately explain Rehoboth Beach when Sea Witch Festival takes over town.
Costumes. Bands. Floats. Dogs in costumes. Activities. Vendors. Music. Kids everywhere. Adults dressed like kids. Kids dressed better than the adults.
The 2026 festival runs October 23–25, with the huge Sea Witch Parade moving down Rehoboth Avenue on Saturday, October 24.
See official Sea Witch Festival information
Dewey gets involved too with trick-or-treating and its Haunted Bonfire and Haunted Graveyard Spectacular during Sea Witch weekend.
Our advice for Sea Witch is simple:
Book the room before you start planning everything else.
Why We Love October at Canalside
October gives you a completely different Rehoboth.
You can put on a sweatshirt and walk the beach. Bring your dog. Bike into town. Spend the afternoon in Lewes. Hear live music at night. Come back for a hot tub and call it a very good day.
Canalside is less than a mile from the beach and boardwalk and gives you complimentary parking, bikes, beach equipment and a quieter place to come back to after the crowds.
Explore our 13 Canalside Inn rooms
Staying into the fall? Our November events guide picks up right where October leaves off.
Summer gets most of the attention.
October has earned some of it back.
Stay Local. Stay Comfortable. Stay Canalside.
