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Downtown Events

Upcoming Events

E.g., Nov 15 2019

Exactus Free Friday Concerts @ Old School Square Pavilion

Fri, 10/04/2019 to Sat, 04/11/2020
On Fridays, enjoy a FREE concert at the Pavilion at Old School Square. With a variety of entertainment options throughout the...

Women Small Business Owners in Pineapple Grove present the 1st ANNUAL WINE WALK!

Tue, 11/19/2019
SAVE THE DATE!! Tuesday, NOVEMBER 19th - 5pm - 9pm 1st ANNUAL WINE WALK Join your Local Pineapple Grove Women Owned Businesses....

33rd Annual Turkey Trot 5K

Sat, 11/23/2019
The City of Delray Beach is excited to host the 33rd Annual Turkey Trot 5K Run/Health Walk on November 23, 2019 at Anchor Park....

Beyond Basel at Cornell Art Museum

Wed, 12/04/2019
Artists, gallerists and art collectors from around the world will visit South Florida for art week, and we’re bringing the...

Annual Boynton Beach & Delray Beach Holiday Boat Parade

Fri, 12/13/2019
The Boynton Beach Community Redevelopment Agency and the City of Delray Beach invite you to celebrate the holiday season Florida...

Delray Beach Winter Green Market

Sat, 10/26/2019 to Sat, 05/16/2020
The GreenMarket is a Saturday morning destination as an open air marketplace located at Old School Square Park on NE 2nd Avenue,...

An Olde Fashioned Holiday

Thu, 11/21/2019 to Sat, 11/23/2019
The Southern Handcraft Society, Pineapple Grove Chapter, Delray Beach, will hold its 27th annual, juried art and craft show, An...

20th Annual Downtown Delray Beach Thanksgiving Weekend Art Festival

Sat, 11/30/2019 to Sun, 12/01/2019
This annual juried art festival of hand-crafted artwork including glass, photography, painting, mixed media, fiber, jewelry and...

3rd Annual Delray Beach Pickleball Classic

Thu, 12/05/2019 to Sun, 12/08/2019
Join the Delray Beach Pickleball Club for this fun event! Bring the family too. This ievent is FREE for all spectators! Enjoy the...


Tue, 12/31/2019
The concert celebrates the life and career of the disco Queen, Donna Summer, from the mouth of her very own sister and back-up...

65 roses - Evening on the Ave

Fri, 11/15/2019
The Cystic Fibrosis Foundation is excited to invite you to be a part of 65 Roses Evening on the Ave. Taking place at Old School...

Chris Evert Pro-Celebrity Tennis Classic

Fri, 11/22/2019 to Sun, 11/24/2019
Join Chrissie at the Delray Beach Tennis Center for two fun-filled days of great tennis action. Each year, well-known...

Small Business Saturday

Sat, 11/30/2019
Take the Pledge and #ShopSmall on Small Business Saturday in Downtown Delray Beach, Saturday, November 30th! Hundreds of unique...

100 Ft Christmas Tree & Holiday Festivities

Thu, 12/05/2019 to Wed, 01/01/2020
December 5th, 2019 – 100 ft Christmas Tree Lighting Ceremony -  5:30 p.m. to 9 p.m. Start the holiday season off in Delray Beach...

31st Annual Downtown Delray Beach Festival of the Arts

Sat, 01/18/2020 to Sun, 01/19/2020
The Downtown Delray Beach Festival of the Arts, consistently ranked as one of the best art affairs in the U.S. by Sunshine Artist...

Upcoming Downtown Events

Fashion Bowl 54

6:00pm - 10:00pm

Atlantic Avenue in front of The Colony Hotel, 525 E Atlantic Avenue, Delray Beach. Ticketed runway seating, entertainment, dance party,...

Old School Square Super Pep Rally

6:00pm - 10:30pm

Old School Square Park and Pavilion, 51 N. Swinton Avenue, Delray Beach. A FREE pep rally and concert pre-Super Bowl community event...

Annual Thanksgiving Weekend Art Festival

10:00am - 5:00pm

This annual juried art festival of hand-crafted artwork including glass, photography, painting, mixed media, fiber, jewelry and much...



This flotilla of brightly-decorated boats can be viewed from Veterans Park and Knowles Park and along the parade course that starts in...


5:00pm - 9:00pm

Delray Beach will ring in the New Year on December 31st with a family friendly event from 5-9pm.

Location: Old School Square...

Art Couture All-Stars

7:00pm - 10:00pm

Cornell Art Museum at Old School Square, 51 N. Swinton Avenue, Delray Beach. The Delray Beach local fashion designers present their...

Downtown Shop the Runway Blitz

10:00am - 3:00pm

Shop participating retailers within downtown Delray Beach - back by popular demand! Attendees will enjoy a welcome reception, Fashion...

Holly Jolly First Friday Art Walk

6:00pm - 9:00pm

The First Friday Art Walk is a perfect way to experience an evening of art, education, and relaxation in our award-winning Arts Town....

Delray Beach Holiday Parade


With over 70 entries in the parade to help you celebrate the holidays. Through a special connection to the North Pole, The Delray Beach...

Halftime & High Heels Luncheon Fashion

11:30am - 2:30pm

CHE!!! Restaurant, 900 E Atlantic Avenue, Delray Beach
Luncheon, resort wear fashion show with over 70 looks, entertainment,...

Celebrate The Big Game 2020


Throughout Downtown Delray Beach
Celebrate Super Bowl 2020 Sunday throughout downtown Delray Beach with shopping, trunk shows,...

Carols by Candlelight


Young, local performers will open the festivities, followed by special guest performances and headlined by Gloria Gaynor! The event...



Lighting of the first candle of the Menorah on the grounds of Old School Square.

Time: Sundown
Location: Old School Square...