Shop Small at Downtown Delray Beach this Holiday Season!


Join in the spirit of this magical season with a celebration of holiday cheer!  Downtown Delray Beach is the perfect destination for Very Merry Mondays, live entertainment, and beautiful décor from twinkle lights and wreaths, to store windows and a 100 ft. lighted holiday tree.

Delray Beach Ornament Giveaway | EXTENDED through December 21st
Spend $200 at Downtown Delray businesses and receive an exclusive Delray Beach 2020 Holiday Ornament! Receipts must be from a downtown Delray Beach business with purchase made between Nov 27th and December 21st.  Redeem ornaments on Very Merry Mondays (see information below on locations & times).
*Receipts on food & beverage, transportation & parking, Green Market or accommodations not applicable. 
For more information, click here. 
Very Merry Mondays | November 30 - December 21
Head to Downtown Delray Beach on Mondays for some Holiday Cheer!  Throughout the holidays, every Monday from 4-7pm, Downtown Merchants and the DDA will celebrate the season in a different neighborhood. We welcome guests to bring a toy for the Delray Beach Toy Drive and in exchange will receive Secret Santa tickets for a chance to win some goodies to Downtown Delray.  We hope you stay awhile to get to know & shop local merchants while enjoying festive entertainment and treats!
Dates and locations:
Mondays from 4pm - 7pm
11/30 | East Atlantic Avenue Stroll (Swinton to 6th Avenue) 
12/7 | West Atlantic Stroll (I-95 to Swinton)  
12/14 | Beachside Stroll (6th Avenue to A1A)
12/21 | Pineapple Grove Stroll (NE 2nd Avenue and North)
View all of the Very Merry Monday event information, click here.
Downtown Delray Beach Businesses: sign up here for Very Merry Mondays!
Festive Holiday Street Decor in Downtown Delray and the 100 ft. Christmas Tree | December 1 - January 1
NOTE: The 100ft Christmas Tree lighting ceremony has been put on pause. The tree is LIT, so come out and join us at Very Merry Mondays and see the tree!
Visit downtown Delray Beach to get in the spirit of the season from festive Holiday Decor & lighting to our 100 ft. Christmas Tree, the CHEER is HERE for the month of December! 
About the 100 ft. Christmas Tree:
One of the best trees in the USA - For 26 years, Delray residents and visitors alike have marveled at our Famous 100 Ft Christmas Tree. In 2016 it was named by Travel & Leisure the best Tree in the state of Florida, right up there with the trees at Rockefeller Center and the White House. Building the Tree is a month-long community event that brings together people of all ages and all walks of life. 
*This year the Tree interior will be closed due to COVID-19, however you can still visit and marvel at the light and joy this massive tree brings to the season! 
Downtown Holiday Window Decorating Contest | December 1 - December 24, 2020
Downtown Delray Beach is hosting a Holiday Décor Window Contest and businesses are creating festive displays in their windows and throughout their stores.  Stroll downtown from December 1 – December 20 and vote for your favorite merchant for the #peopleschoiceaward.  A panel of Judges will also vote on different categories.
Top businesses will receive prizes based on the following categories (voted on by a panel of judges):
Best Overall: $500
Most Festive: $200
Most Delray: $200
Most Creative: $200
Prize for best decorations voted on by the public:
People's Choice Award: A One night stay at the Seagate Hotel in deluxe accommodations plus a round of golf at the Seagate Country Club
Voters you have a chance to win just for voting! 
Vote for your favorite decorations (VOTE HERE& enter in a chance to win:  A brunch for two at Atlantic Grille (appetizer, entree, mimosa)
Downtown Delray Beach businesses, sign up for the Holiday Window Decor Contest HERE
Check out all the contest participants and cast your vote:

Check back for more information regarding upcoming Holiday Festivities & Events in Downtown Delray Beach!

Looking for the perfect gift?  Check out our Downtown Delray Beach Gift guides to shop local treasures: 

*The photographs below are compliments of Carl Dawson, VMA Studios. 


CANCELLED - Holiday Boat Parade
Fri, 12/11/2020

As a precautionary measure to prevent the possible spread of COVID-19, the BBCRA has made the difficult decision to cancel the 49th Annual Boynton Beach & Delray Beach Holiday Boat Parade event, which was scheduled to take place on Friday December 11, 2020.

Letters From Santa
Wed, 11/11/2020 to Fri, 12/18/2020

The City of Delray Beach will deliver your letter directly to Santa Claus. From now until December 18, write a letter to Santa, drop it off* in the North Pole Mailbox located at the Community Center, Pompey Park, or Catherine Strong Park, and we will make sure Santa receives it!!

"Delray Memories" - 100 years of History
Mon, 11/16/2020 to Thu, 12/31/2020
9:00am - 7:00pm

The "Delray Memories" Exhibit is OPEN through December 31st, 2020. You can meander through our one-acre campus and gardens and enjoy this unique outdoor exhibit featuring over 1,000 fascinating and heartfelt images capturing 100 years of local history. It is FREE and open 7 days a week, 9 am - 7pm.

Ugly Sweaters in the Snow!
Sun, 11/29/2020
5:00pm - 7:00pm

On November 29th 5-7PM say hello to the official holiday season! Our snowmen will make it snow in Delray and whoever dons the ugliest sweater will win $25 and a bottle of cheer!
Email to book large groups, inquire about or to-go holiday egg nog and cocktail party packages

12 Days Of Christmas Sales
Tue, 12/01/2020 to Sat, 12/12/2020

From December 1st to December 12th don't miss out our "12 Days Of Christmas Sales"!!

Take 20% OFF listed items on designated day!

Christmas with The Nelsons
Sat, 12/05/2020

Join us for the 5th Annual Carols by Candlelight holiday concert featuring Matthew & Gunner Nelson of THE NELSONS!

Big Bad Voodoo Daddy: Wild and Swingin'
Fri, 12/11/2020

Get in the holiday spirit with Big Bad Voodoo Daddy's one-of-a-kind Wild and Swingin' Holiday Party!

2nd Annual Tacky Holiday Barre Class
Thu, 12/24/2020
8:30am - 12:00pm

Our 2nd annual Tacky Holiday Barre Class takes place during ALL morning classes Thursday December 24. Join in on the tacky fun both online and in person(livestream class at 9:45am only) Wear your favorite tacky holiday workout attire for a chance to win a VERY VERY MERRY Prize package!

Season's Celebrations at the Cornell
Fri, 11/27/2020 to Sun, 01/03/2021
12:00pm - 5:00pm

Step into a winter wonderland and experience immersive installations, see artwork by internationally known contemporary artists, and do some holiday shopping in our Museum Store!

Artists: Alex Beard, Michelle Drummond, Pati Maguire, Amanda Perna, Elaine Prather, Jonathan Rosen, Brenda Zapittell

It's the hottest Year-End Sale!
Tue, 12/01/2020 to Thu, 12/31/2020

Get your next look while you still can from Aqua and Etc. Gifts at The Seagate Hotel!!

We are having our year-end retail sale happening all month long with 50% just about all merchandise.
Just in time for the holidays!!

** In stores only while supplies last. Some exclusions apply.

Tuesday, December 1, 2020 to Friday, January 1, 2021
Downtown Delray Beach Delray Beach, FL