Sunset & Chill (Fri)

Hours: 6p-10p

Where: Cranes Roost Park

Information Provided by DELTA SIGMA THETA SOROTIY, INC.

Tickets

The wait is over! Back again by popular demand for the fourth annual Sunset & Chill Scholarship Fundraiser hosted by Sanford And Orlando Entertainment & The Sanford Alumnae Chapter of Delta Sigma Theta Sorority, Inc.

Join us at Cranes Roost Park for an unforgettable experience with live music from L8est Edition and special guests. As the sun sets, you’ll enjoy smooth rhythms, food trucks and an array of vendors. Get your dancing shoes ready!

New this year, VIP tables of four seats are available.

Dress to impress and don’t forget your lawn chairs!
Looking forward to Sunset & Chilling with you!

$40 Early Bird Tickets are available until March 31, 2025.


Rocking on the River Cinco De Mayo (Fri)

Hours: 6:30p-9:30p

Where: Sanford Marina - Barbara Lee

Information provided by St. Johns Rivership Co.

Join us for an unforgettable Cinco De Mayo celebration aboard the Barbara Lee, featuring the electrifying beats of DJ Ernie. Cruise along the scenic St. Johns River and dance the night away to your favorite songs. Enjoy breathtaking views, including stunning Central Florida sunsets, from the outer viewing decks and the covered paddlewheel deck. The inside area is fully enclosed and climate-controlled for your comfort.

Admission is just $25 per adult, with an à la carte menu and a full bar available for purchase. Don’t miss this incredible party cruise experience. Get your tickets now by calling our office at 321-441-3030 or visiting RivershipTix.com.


Mom’s, Merchants & Mimosas (Sat)

Hours: 10a-2p

Where: My Oviedo Store

Information provided by My Oviedo Community

Our annual Moms and Mimosas is here! Join us Saturday May 3rd for our annual event where local merchants bring you great gifts for Mother's day, along with My Oviedo Store offering free mimosas while you shop!


Longwood Luau (Sat)

Hours: 4p-8p

Where: Reiter Park

Information Provided by: City of Longwood

Join us on May 3, 2025, at Reiter Park for the Longwood Luau!

Live Hawaiian Music
Hula Dancers
Fire Knife Performers
Traditional Hawaiian Foods
Tropical Drinks
Hula Hoop
Limbo

And much much MORE!

** TENTS AND UMBRELLAS WILL NOT BE ALLOWED ON THE AMPHITHEATER LAWN. ONLY CHAIRS, MATS AND BLANKETS WILL BE ALLOWED FOR EVENT.

* NO DOGS ALLOWED IN REITER PARK

Sanford Food Truck Fiesta: Cinco De Mayo Block Party (Sun)

Hours: 1p-6p

Where: Historic Downtown Sanford

Information provided by: City of Sanford

SANFORD FOOD TRUCK FIESTA: CINCO DE MAYO BLOCK PARTY!

Spice up your weekend plans and join us Saturday, May 4th from 1–6PM in the heart of historic downtown Sanford for a fiesta you won’t forget! We’re bringing the flavor, the fun, and the full-on block party vibes to celebrate Cinco de Mayo — Sanford style!

40+ Food Trucks!
Live Mariachi Band!
Live Music by Stereo FM!
Craft Beer. Cocktails and Non-Alcoholic Bevs!
Family & Pet Friendly!
Plenty of Outdoor Seating!
Vendors + Free Parking!

Whether you’re chasing tacos, churros, cold brews or live tunes, this block party's got it all!

Here is a current list of the amazing food trucks and tents participating in the month of May:

Ravoliscious
Rineboi Churrasaco Grill
One Way Coffee
S Treats & Coffee
Wild Thorne Dairy
Chonky's Kitchen
GoJuice Debary
The Knot
Dani mini O's
Da Bronx N.Y. Street Food
Papa Diesels BBQ
Asian Street Eats, FL
Grandma's BBQ
Preciosa Subs + More
The Tea Lizard
Oh My Dogs
The Pass Progressive Cuisine
Olive & Feta Grill
Fat Boi Gourmet Potatoes
Loco Burgers
Oishiimotto Japanese
Island Life Cuisine
BBQ Brazil Express
Gaucha Argentine
Churros and Cream
The Real Maine Lobster
American Stadium Grill
Baohouz
Popcorn Fix
The Hook Orlando
Chikiz empanadita
La Parada de Tacos
Smoothie Express
GringaMex
Alaskan Ice
Honey Badger Treats
Jersey Family Grill
Mama Cannoli
Magdalena’s Chimney Cakes

Tag your crew, bring the fam, leash up your pup, and get ready to eat, drink, and dance your way through downtown Sanford!

Huge gracias to our amazing sponsors who make this celebration possible:
Ladies 327, The West End Trading Co., The Joint at West End, Celery City Craft, Celery City Cigars, Wild Wild West End Saloon, Maya Rosa, Decision Tactical, Power Home Remodeling, The Station Bar & Grub, and Hot Asian Buns!

You bring the appetite—we’ll bring the fiesta. See y’all May 4th!

And if you’re looking for things to do year round, check out our other blog!

Free and Budget Friendly Things To Do in Central Florida