October is one of our favorite times of year in Rehoboth Beach – and Jazz Fest weekend makes it even better.
The 37th annual Rehoboth Beach Jazz Festival returns October 15-18, 2026, bringing four days of smooth jazz, R&B, funk and nationally known performers to stages in Rehoboth Beach, Lewes and Dewey Beach.
And if you have been thinking about coming this year, here is the good news. Canalside Inn still has rooms available for Jazz Fest weekend.
Rehoboth Beach Jazz Festival 2026 at a Glance
- Dates – Thursday, October 15 through Sunday, October 18, 2026
- Where – Venues across Rehoboth Beach, Lewes and Dewey Beach
- Headliners – Boney James, Brian Culbertson, Najee, Gerald Albright, Damien Escobar, Acoustic Alchemy and many more
- Tickets – Sold show by show through the official festival website
- Free music – Reggie Harris plays the Historic Lewes Farmers Market on Saturday morning
- A good cause – The festival gives back each year to the Tunnell Cancer Center at Beebe Healthcare
A Big Weekend of Music at the Beach
What started as an off-season event in 1990 has grown into one of the signature fall weekends at the Delaware beaches. The lineup leans toward contemporary and smooth jazz, with plenty of R&B and funk mixed in, and many of the artists show up on more than one stage over the weekend.
The 2026 lineup includes
- Damien Escobar with Peter White and Vincent Ingala, opening the festival Thursday night
- Boney James on Friday night at the Convention Center
- Brian Culbertson twice on Saturday, with a solo set in the afternoon and a full show that night
- Gerald Albright with Keiko Matsui and the Eboni Strings
- Najee with special guests Regina Belle and Alex Bugnon
- Acoustic Alchemy, Walter Beasley, Stanley Jordan and Diego Figueiredo
- Brian Simpson, Jessy J and Marion Meadows, who also anchor the 2026 Rehoboth Beach All-Stars
- Paul Taylor and Michael Lington at the Rusty Rudder in Dewey Beach
- The Grand Jam on Sunday, the festival’s signature closing jam session
2026 Jazz Fest Schedule Highlights
Here are the shows we would build a weekend around. Times and venues come from the published 2026 schedule, so double-check the official festival site before you buy, since lineups can shift.
| Day | Time | Performer | Venue |
|---|---|---|---|
| Thursday, Oct. 15 | 7 p.m. | Damien Escobar with Peter White and Vincent Ingala | Rehoboth Beach Convention Center |
| Friday, Oct. 16 | 5 p.m. | Brian Simpson, Jessy J and Jackiem Joyner | Cambria Hotel, Rehoboth |
| Friday, Oct. 16 | 7:30 p.m. | Walter Beasley | Epworth United Methodist Church, Rehoboth |
| Friday, Oct. 16 | 8 p.m. | Boney James | Rehoboth Beach Convention Center |
| Friday, Oct. 16 | 8 p.m. | Marion Meadows and Alex Bugnon | Rusty Rudder, Dewey Beach |
| Saturday, Oct. 17 | 10 a.m. | Reggie Harris (free) | Historic Lewes Farmers Market |
| Saturday, Oct. 17 | 12:30 p.m. | Gerald Albright with Keiko Matsui and the Eboni Strings | Rehoboth Beach Convention Center |
| Saturday, Oct. 17 | 1 p.m. | Brian Culbertson (solo) | Epworth United Methodist Church, Rehoboth |
| Saturday, Oct. 17 | 4 p.m. | Najee with Regina Belle and Alex Bugnon | Cape Henlopen Performing Arts Theater, Lewes |
| Saturday, Oct. 17 | 4 p.m. | Paul Taylor and Michael Lington | Rusty Rudder, Dewey Beach |
| Saturday, Oct. 17 | 5 p.m. | Stanley Jordan and Diego Figueiredo | Cambria Hotel, Rehoboth |
| Saturday, Oct. 17 | 7:30 p.m. | 2026 Rehoboth Beach All-Stars | Cape Henlopen Performing Arts Theater, Lewes |
| Saturday, Oct. 17 | 7:30 p.m. | Acoustic Alchemy | Epworth United Methodist Church, Rehoboth |
| Saturday, Oct. 17 | 9 p.m. | Brian Culbertson | Cape Henlopen Performing Arts Theater, Lewes |
| Sunday, Oct. 18 | 3:30 p.m. | 2026 Grand Jam | Rehoboth Beach Convention Center |
| Sunday, Oct. 18 | 6:30 p.m. | Closing Party Buffet | Rusty Rudder, Dewey Beach |
Night owls should also know about the late sets at the Cambria Hotel on Friday and Saturday, which keep the music going well after the main shows let out.
How to Plan Your Jazz Fest Weekend
With shows in three towns, a little planning goes a long way. A few things we tell our guests every October
- Buy tickets for the big rooms first. The Convention Center and Cape Henlopen shows are the ones most likely to sell out.
- Group your shows by town. Saturday works beautifully as a Lewes day, with the free morning set at the farmers market and the afternoon and evening shows at Cape Henlopen just a few minutes away.
- Plan to drive to Lewes and Dewey. Rehoboth venues are an easy hop from the inn, but you will want the car for Cape Henlopen and the Rusty Rudder. Free parking at Canalside means you are not hunting for a spot when you get back.
- Book dinner early. Restaurants fill up before showtime. Our Rehoboth Beach dining guide and our day-by-day guide to restaurant specials are good places to start.
- Bring layers. October afternoons are often mild, but evenings cool off quickly near the water.
A Sample Jazz Fest Weekend
- Thursday – Arrive, check in and walk or bike into town for the opening night show at the Convention Center.
- Friday – Take a slow morning on the beach, have lunch downtown, then head to Boney James at the Convention Center or Marion Meadows at the Rusty Rudder.
- Saturday – Spend the day in Lewes, starting with the free farmers market set and finishing with Najee or Brian Culbertson at Cape Henlopen. If you have time between shows, our guide to off-season restaurant deals in Lewes comes in handy.
- Sunday – Sleep in, grab brunch and catch the Grand Jam before heading home.
Jazz Fest Weekend Feels Different All Over Town
One of the reasons we love Jazz Fest weekend is that the whole area changes.
You can catch a show, grab dinner downtown, walk Rehoboth Avenue, stop in for a drink and spend some time by the water. Add an hour on the Rehoboth Beach boardwalk and the festival turns into a real fall getaway. If you end up in Dewey for a show, our list of Dewey Beach bars will help you pick a spot before or after.
October is also a wonderful time to experience Rehoboth Beach without the peak-summer crowds. The weather is cooler, downtown is still active, and many of our favorite restaurants, shops and local businesses are open.
There is plenty of other music in town that week too. True Blue Jazz runs its own festival programming in Rehoboth and Lewes October 14-18, and the CAMP Rehoboth Block Party takes over Baltimore Avenue on Sunday, October 18. Our October events guide for Rehoboth Beach has the full rundown.
And yes – the beach is still beautiful in October. Leashed dogs are welcome on the beach and boardwalk this time of year when lifeguards are off duty, so your pup can come along for the morning walk. We keep a longer list of dog-friendly fall activities in Rehoboth Beach if you are making a weekend of it with your dog.
Make Canalside Inn Your Jazz Fest Home Base
Canalside Inn gives you a quieter place to relax between shows while keeping you close to everything happening in Rehoboth, Lewes and Dewey.
We are tucked along the Lewes-Rehoboth Canal, about a mile from the beach and boardwalk. Close enough to enjoy downtown, and far enough from the busiest parts of town when you are ready to unwind.
During your stay, you can enjoy
- The outdoor hot tub, which is just right after a long night of music in the October air
- Complimentary bikes for getting downtown without moving the car
- Free parking for one vehicle per room
- Coffee and Wi-Fi to get the morning going
- In-room mini fridges and microwaves for leftovers from that dinner you could not finish before the show
- Outdoor gathering space along the canal
- Dog-friendly rooms with welcome treats, towels and an outdoor rinse station, so your four-legged family member can come too (see our pet-friendly stay details)
You can see the full list on our amenities page. Celebrating something during the trip? An in-room massage package makes a pretty good encore.
Spend the afternoon exploring Rehoboth, head out for your evening concert, and come back to somewhere that feels a little more like home than a traditional hotel. If you are weighing your options, here is our honest take on a boutique hotel vs. an Airbnb in Rehoboth Beach.
Don’t Wait Until Jazz Fest Weekend to Find a Room
Jazz Fest traditionally brings thousands of visitors to the Delaware beaches, and rooms get harder to find as the weekend gets closer.
We still have availability October 15-18, which makes now a great time to plan a last-minute Jazz Fest getaway. Coming in from out of town? Our getting here guide and our tips for getting from the Philadelphia airport to Rehoboth will help.
Pick the concerts you want to see. Make a dinner reservation. Pack something warm enough for an October evening by the water.
We will take care of the place to stay.
Ready for Jazz Fest?
Check the complete 2026 schedule and buy concert tickets through the official Rehoboth Beach Jazz Festival website.
Then book your stay directly with Canalside Inn and make a weekend out of it.
Jazz. The beach. Great food. Fall in Rehoboth.
Sounds like a pretty good October weekend to us.
