On the Road Again returns Oct. 4

On the Road Again returns Oct. 4
By Jake Spitzack | Staff Writer | October 2025

Fall fun kicks off this year Saturday, Oct. 4 with the city’s annual On the Road Again festival, featuring the beloved annual Booyah contest, car show, chalk-art competition and much more. Events run 9 a.m.-6 p.m. along Southview Boulevard and side streets. The festival was first organized in 1988 to celebrate the completion of a 2-year street, water and sewer project on Southview Boulevard. Business owners held the event to thank the community for supporting them during construction and it evolved into an annual event. Details of this year’s festivities follow. Information was accurate as of press time.

on the road again 2025 — Booyah World Championship, 11 a.m. until the last ladle is dished out.

Arts and Crafts Flea Market, 8 a.m.-5 p.m.
More than 100 vendors will offer bargains on vintage and handcrafted items.

Booyah World Championship, 11 a.m. until the last ladle is dished out. Community chefs use secret recipes to prepare a combined 800-1,000 gallons of stew as they compete for trophies and bragging rights. Sample their concoctions then cast your vote. Judging begins at noon. Last year’s winner was Booya Crew. For more details, contact Brenda at 763-228-9470.

Chalk Art Competition returns for its third year at 4th Avenue and Southview Boulevard. Approximately 20 artists from around the metro area and a few from Iowa, Nebraska and South Dakota will create chalk art in 7-square-foot spaces 8 a.m.-3 p.m. The public will cast votes for the winners, and judging will take place 3-3:30 p.m. First place winner will receive $350, second place $250, and third place $150. The winner of the “festival favorite” design will also get $350. The event also features a kids’ zone where children can help create a chalk mural.

Cool Truck and Bass Boat returns for its second year. Professional bass fisherman Tyler Darrow will teach children casting techniques 9 a.m.-2 p.m. at Southview 66, 725 Southview Blvd. Free.

Giant Medallion Car Show, 10 a.m.-4 p.m., between 9th and 12th avenues and side streets. Check out the wide array of vintage cars and trucks flaunting dazzling paint jobs, custom and classic designs and other meticulous works of restoration.

Little Elko Quarter Midget Race Cars returns for its second year. Cars will be on display at Southview 66, 725 Southview Blvd.

South St. Paul Lions Club Beer Garden and Raffle, 11 a.m.-5 p.m., at 9th and Southview. Quench your thirst at the Lions Club beer garden and take part in their raffle drawing at 2:30 p.m.

Live music, noon-4 p.m., at 8th Avenue and Southview Boulevard. Vivian Hayes will perform. Food, face painting and kids’ activities will be featured throughout the festival area.

Pickle Contest, judging begins at 2 p.m. Sample homemade pickles and cast your vote for the best. Contestants will compete in three categories: sweet, dill and hot. To enter the contest, drop off your pickles by 11 a.m., Saturday, Oct. 4 at Southview 66, 725 Southview Blvd. Last year had 24 entries and the winner was Peggy’s Pickles.

St. Paul Fall Art Crawl, Oct. 10-12. See full details here!
More Fall Events here!

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