From Dueling Jazz Festivals to Flying Pups, it's a Great Weekend to be in Rehoboth Beach

October 13, 2021

If you've been following our coming events blog over the last few weeks, then you get the drill - It's fall festival season throughout the region!

This time of year never disappoints, with fun, family-friendly events and festivals around every turn. And this weekend is certainly no different, with another jam packed schedule of great things to do in the coastal region and beyond.

The weather is beginning to turn cooler and, before you know it, Old Man Winter will be making his annual house call. But before his inevitable arrival, get outside and enjoy yourself at one or more of the great events coming up this weekend.

We're going to begin in Delaware's favorite and most popular coastal resort of Rehoboth Beach, but there's no shortage of things to do this weekend no matter where you live or happen to be visiting.

Whatever you end up doing, make it a fantastic and memorable weekend!

Rehoboth Beach Jazz Festival (October 14-17)

The “Nation’s Summer Capital” will be filled this weekend with the smooth sounds and easy listening of some of the area’s finest jazz music.

This year welcoming 2021 Artist of the Year Maysa, along with favorites like Art Sherrod, Jr., Mindi Abair, Joey Alexander and many more, the 2021 Rehoboth Beach Jazz Festival is held over four days and at various locations throughout Rehoboth and Dewey Beach.

This popular annual event always brings record crowds to coastal Delaware, with many nationally known jazz musicians, as well as countless local favorites, taking the stage each year.

Shows for 2021 will be held at several different sites, including the Cape Henlopen Performing Arts Theatre, the Rehoboth Beach Convention Center, the Rusty Rudder and Epworth United Methodist Church.

Plus there will also be many local restaurants and bars offering great entertainment. For the full schedule and list of performers this year, visit

True Blue Jazz Festival (October 13-17)

For the ninth consecutive year, this independent jazz festival will be again be held in the middle of October in the “Nation’s Summer Capital” of Rehoboth Beach.

Produced by Eddie Sherman and Nassau Valley Vineyards Owner Peggy Raley, this event focuses on mainstream jazz music, featuring songs from 1900 to today.

The event for 2021 is now five days and will be held between Wednesday, October 13 and Sunday, October 17. The main venue in Rehoboth Beach will again be the showroom at the Boardwalk Plaza Hotel, but several other venues will also be hosting performances, both live and virtual.

Other venues in Rehoboth Beach include The Pines, Port 251, the Ocean Glass Inn, Left's Alley & Eats and Aqua Bar & Grill, among others. Click here to learn who will be performing at these venues throughout the five days of the event.

To learn more about the 2021 True Blue Jazz Festival, visit

Bark on the Boards (October 16)

Rehoboth Beach is once again going to the dogs this weekend, but this time it's in the form of a block party that everyone in the family is sure to enjoy.

Scheduled for 10 a.m. to 1 p.m., on Saturday, October 16, the 2021 Bark on the Boards will be held in the area of the Rehoboth Beach Bandstand and feature a number of family-friendly activities.

Included during the course of the three-hour event will be a special walk on the Boardwalk, a pet costume contest, games and inflatables for the kids, a chance to do yoga with your pet, a festive drag show featuring the one-and-only Magnolia Applebottom and the special Dock Dogs diving competition, which is always a hit with the public.

Click here for more information on the 2021 Bark on the Beach event in Rehoboth Beach.

Click here for the rest of this weekend’s busy events calendar

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