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Dueling Jazz Festivals and a Springtime Favorite Offer Great Opportunities for Mid-October Fun at the Beaches

October 14, 2020

Be prepared for hundreds of bicycles on area roadways this weekend as one of the biggest events of the Spring will be taking place in the coastal region. No, it’s not a typo. We did actually say Spring, and we meant it.

The 31st Annual Ocean to Bay Bike Tour will be taking place this Friday and Saturday. It’s an event that’s normally held every April, but for 2020 is occurring in the Fall because of the coronavirus related shutdown a few months ago.

It’s actually one of several noteworthy events we’ll be telling you about this week, as both the Rehoboth Beach Jazz Festival and the True Blue Jazz Festival are also being held, albeit in scaled down versions compared to past years.

Add in a fun Halloween themed event in Ocean City and the latest lineup at the fabulous Milton Theatre and you many options for a fun-filled weekend at the Delaware and Maryland beaches.

Read below for much more on this weekend’s featured Oldfather Group events. We begin in Rehoboth Beach…

True Blue Jazz Fest (October 15-18). For the eighth consecutive year, this independent jazz festival will be going on as planned 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 2020 will be a mixture of live music and virtual events, held between Thursday, October 15 and Sunday, October 18. The main venue in Rehoboth Beach will again be the showroom at the Boardwalk Plaza Hotel, where live jazz will be streamed on both Friday and Saturday evenings.

Other venues in Rehoboth Beach include The Pines, Port 251, the Ocean Glass Inn and Aqua Bar & Grill. Click here to learn who will be performing at these venues throughout the four days of the event.

Acts this year include both local and regional jazz musicians, as well as nationally and internationally recognized icons of the industry. Headliners that were scheduled for 2020, however, have been rebooked for 2021.

To learn more about the 2020 True Blue Jazz Festival, visit www.truebluejazz.org.

Ocean to Bay Bike Tour (October 16-17). Normally held every year in April, this popular and award-winning annual event was postponed due to the coronavirus pandemic but is now rescheduled for this Friday, October 16, and Saturday, October 17.

This is the 31st year that the event’s been held in coastal Delaware, which usually brings around 2,500 cyclists to the area. Again presented by the Bethany-Fenwick Area Chamber of Commerce, cyclists can chose between 30 mile, 50 mile and Metric Century (62.5 miles) routes.

Because COVID-19 is still a concern, cyclists have the option of participating in the in-person event or choosing a virtual option and completing a route of their choosing. There’s also a 10 mile “Coastal Cruise” planned for Friday that will start in downtown Bethany Beach and conclude at the Big Chill Beach Club at Delaware Seashore State Park.

Saturday’s start times for the in-person events range from 7 to 9 a.m., depending on which course is chosen. Friday’s casual ride to the state park is scheduled for 12 to 4 p.m.

Learn more about this year’s Ocean to Bay Bike Tour at www.oceantobaybiketour.com.

Mini Jazz Fest (October 16-18). The 2020 Rehoboth Beach Jazz Festival is not being held as planned in 2020 due to current health mandates in Delaware. But organizers are holding a “Covid Be Damned” mini jazz fest in its place, with five performances planned between October 16-18.

Billing this year’s scaled back event as “music for the cure,” shows will be held at Sydney’s Restaurant in Milton and on the deck at the Rusty Rudder in Dewey Beach.

Masks must be worn at the Rudder while moving around, but can be removed while seated and watching the show. Official jazz festival masks will be provided for those attending performances at the Rusty Rudder.

Performers for this year’s event include Marcus Anderson, Art Sherrod, Jr., Maysa and Sax & Tracks.

Visit www.rehobothjazz.com for more information.

Click here for more of this weekend’s featured events

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