Englewood Pioneer Days

The celebration brings a parade, two-day festival and more to Englewood over Labor Day weekend

Englewood Pioneer Days’ 61st annual

celebration started last weekend with events including ChalkFest. Yet the largest festivities, including the free two-day festival and parade, take place over Labor Day weekend.

Here’s a schedule of the Englewood Pioneer Days events happening this weekend. For more information, visit englewoodpioneerdays.com.

Cardboard Boat Race: 9 a.m., 11 a.m. race start Saturday; Indian Mound Park; $10-$30 entry fee, free spectators

Kids and adults alike can build boats made out of cardboard, then paddle or sail it on a Lemon Bay course just off the southern tip of Indian Mound Park. The race has three classes: Prams (10 years old or under, $10 entry fee), Sunfish (11-15 years old, $20) and World Cup (all other entrants, $30). Registration can be done online or the morning of the race.

Shipwreck Dance: 5-10 p.m. Saturday; Pioneer Park; free

Come in your best “shipwreck” attire reflecting the theme of “Beach Party Englewood Style” for this free event with music, food trucks, costume contest and beer garden. Sheena Brook, a Fort Myers Beach singer who competed on NBC’s “The Voice,” will perform from 6-7:30 p.m., with Englewood Drum Circle kicking things off at 5 p.m. Lawn chairs and blankets are welcome, but coolers and outside food or drinks are not.

Diaper Derby: 2 p.m. race start Sunday; Lemon Bay Woman’s Club; free

Babies can compete in this crawling-only race held at Lemon Bay Woman’s Club. Registration is required by Friday and reservations are requested.

Pioneer Days Festival Day 1: noon-8 p.m. Sunday; Pioneer Park; free

The two-day festival features music, food, a free kids zone, car shows, contests and more. Sunday’s schedule includes O.C.D. Band (noon), Eve Was Framed (1 p.m.), Seamus McCarthy Band (2 p.m.), Sarah Hardwig (3 p.m.), Miles Bosworth (3:30 p.m.), Chris Walker Band (4:30 p.m.), Swinging Bridge (5:30 p.m.) and Saint Tone (6:45 p.m.) Open car show awards will take place at 6:30 p.m.

Open Car Show: 2 p.m. Sunday; Pioneer Park; $5 day-of registration

The car show features two classes — before 1970 and after — and awards for cleanest inside and out, most nostalgic, best engine, best interior, coolest paint job, most unusual state issue license plate, one we would most like to cruise in, best theme display, best truck and ugliest truck, as well as mayor’s choice and best of show awards.

61st Annual Parade: 9 a.m. Monday; Dearborn Street; free

The Labor Day parade starts at 9 a.m., rain or shine, along Dearborn Street.

Pioneer Days Festival Day 2: 8 a.m.-3 p.m. Monday; Pioneer Park; free

Monday’s music schedule includes Souls on Soul at 10:30 a.m. and Kenny Rose at 2 p.m. Contests will include pie-eating (12:25 p.m.), photo (12:45 p.m.), watermelon (1 p.m.) and beard (1:20 p.m.) There will be awards given for the parade at noon and for the Corvette car show at 1:45 p.m.

Corvette Car Show: 11 a.m. Monday; Pioneer Park; $5 day-of registration

The all-Corvette show will also feature two classes — C 1-3 and C 4-7 — with awards for oldest, cleanest inside and out, most unusual color, most unusual state issue license plate, one we would most like to own, best for date night, best looking wheels, best use of color, best theme participant and most accessories, as well as mayor’s choice and best of show.