Jesse James Days

Monday, Jul 14, 2025

Various Venues in Garretson, SD

Jesse James Days is three days of fun brought to you by the Garretson Commercial Club, with live music and entertainment, parade, a 5k/10k road race, vendor fair, inflatables, and much more!

Entertainment
Local businesses go all out for Jesse James Days, providing entertainment on Main on Friday and Saturday evenings, and specials all weekend long!

Inflatables, music, a fishing derby, and vendor fair along with many other activities are also offered throughout the event.

Parade
The highlight every year is the Parade that travels north on Main Avenue!

Local businesses, organizations, vintage vehicle enthusiasts, and more are encouraged to drive the parade, which is held Saturday mornings.

Fun for all ages
Whether young or old, Jesse James Days has something for everyone. We offer activities for the whole family!

From School reunions to family reunions, and from toddlers to seniors, all have options for a great time!

Featuring
Car & Motorcycle Show · Inflatables · Fireman’s Pancake Breakfast · Model Trains · Cornhole Tournament · Street Dance · All-Ages Street Dance · Glow Kayak · Parade with Flyover

Schedule of Events:

All Day - Art Trail- Maps available in Visitor Centers, Treasure Chest, Palisades Art Gallery
All Day - Self-Guided Hikes at Devil’s Gulch -Trail Maps available in Visitor Center
All Day - Nature Scavenger Hunt – Family fun art & nature hunt – Pick up forms at Jesse James Country Store
10:00 AM – 4:00 PM - Specials Available at The Treasure Chest (Friday and Saturday only)
10:00 AM – 6:00 PM - Local Artist Showcase at Palisade Art Gallery
10:00 AM – 8:00 PM - Kayak Rental available with Boundless Adventures
Noon – 6:00 PM - Wine tasting at Humble Hill Winery (¾ mile north on Hwy 11)
1:00 PM – 8:00 PM Fr/Sa, 1:00 PM – 5:00 PM Su  Garretson Swimming Pool
Open for family swimming and concessions (closed 5:00 pm – 6:00 pm for break)
4:00 PM – 6:00 PM - Happy Hour atSports Cabin/The Combine II, The Gulch Bar & Grill
5:00 PM – 10:00PM - Dinner Specials at Sports Cabin/The Combine II, The Gulch Bar & Grill

7:30 AM – 11:00 AM - Pancake Feed at the Fire Department
8:00 AM – 9:00 AM - Registration/Sign-in for Jesse James Road Race
7:30 AM – 11:30 AM - All American Blood Drive sponsored by Garretson Fire Department
9:00 AM - Jesse James Road Race begins
Pre-Registration required for a T-shirt, go to www.VisitGarretsonSD.com  
9:00 AM – 5:00 PM - Running Model Trains Displayed at the School
Model Trains HO Scale layout with lots of details.  Kids will be allowed to run the train throttles.
9:00 AM – 1:00 PM - Arts and Craft Vendor Fair in the Legion building
Vendor set up available Friday evening and Saturday morning
9:30 AM - Parade Line-up begins at Essex Street & Center Avenue (just North of Zion Lutheran Church) – Pre-Registration is preferred.  The registration form is on the website at www.visitGarretsonSD.com/jessejamesdays
10:00 AM – 10:30 AM - Storytime at Siouxland Libraries Garretson Branch
10:00 AM – 4:00 PM - Garretson Heritage Museum open
View the 1960’s Garretson Train Room, Jesse James Robbery display, Town of Sherman display, Palisades Flour Mill display, 1st Telephone Co-op display.  Garretson Pottery for sale. FREE popcorn, coffee and cider.
11:00 AM- 1:30 PM - Food Stand to benefit Caring for Carter
11:00 AM - PARADE BEGINS with Airplane Fly-over
DURING PARADE - Jesse James’ Bank Robbery Entertainment in front of the Garretson Heritage Museum (*FIREARMS WARNING)
Noon – 2:00 PM - Kringen Horse ‘n Wagon Rides load at Jaycee’s Complex softball field concession stand
Noon – 3:00 PM - Toddler Train Rides in the Zion Lutheran Church Parking lot
Noon – 3:00 PM - INFLATABLES at the Ball Field ($10 wristbands/$30 maximum per family)
Noon – 3:00 PM - Garretson Firemen offering Shuttle Fire Truck Rides to the Museum (the “1960’s Garretson Train” display), to the Garretson School (Model Train display) and to the Jaycees Complex (inflatables, swimming, entertainment)
Noon – 3:00 PM - Burger Booth with ice cream/cold treats & beverages by Jaycee Complex Picnic Shelter, fundraiser for Zion Lutheran Youth Group
Noon – 3:00 PM - Petting Zoo by Jaycee Complex concession stand, courtesy of Splitrock Hustlers 4-H
Noon – 3:00 PM - Lions Eye Exam Truck by Zion Parking Lot (free eye exams up to age 18)
Noon – 6:00 PM - Wine tasting at Humble Hill Winery (¾ mile north on Hwy 11)
1:00 PM – 4:00 PM - The Silver Creek Mavericks Wild West Show at the softball field
(FIREARMS WARNING)
1:00 PM – 4:00 PM - DJ musical entertainment at the softball field
5:00 PM – 7:00 PM - Family Activities in the Green Space on Main
5:00 PM – 7:00 PM - Street Dance for All Ages with 280 FIFTH Band on Main Ave (free to all)
8:00 PM – Midnight - Street Dance with “Driven” band by The Gulch Bar & Grill ($15/ wristband)

Click here for Parade Registration

Click here for Race Registration


View all events in the Destin area