Kid-Friendly Events

Location: Harrow Fairgrounds, Harrow

Time: Sept. 3: gates/midway 1 PM, 4-H 4 PM, opening 5:30 PM · Sept. 4: Teddy Bear Parade 10:30 AM · Sept. 5: midway 11 AM, parade 11:30 AM · Sept. 6: Family Day

One of Essex County's biggest fall traditions! Kids can enjoy midway rides, 4-H displays, animals, the Teddy Bear Parade, children's entertainment, contests and plenty of fair food. There's also a dedicated "Just for the Kids" lineup with a Children's Pedal Pull, LEGO/k'NEX competition, live entertainment and poster competition. Kids 12 & under are free.

Location: Windsor riverfront

Time: Friday 4 PM – midnight; Saturday–Sunday noon – midnight

A waterfront weekend combining food, music, cultural performances and family entertainment. For kids, the festival includes face painting, mehndi art, a bouncy castle and interactive activity areas. Admission is free.

Location: Downtown Amherstburg

Time: Friday 5–9 PM · Saturday: activities begin 8 AM, music 12–6:30 PM · Sunday: schedule TBA

The final Open Air weekend of the season is a great small-town family outing, with vendors, food, live music and special activities throughout downtown Amherstburg. Saturday features a historical tour at 2 PM and live music from noon into the evening.

Location: Lakewood Park, Tecumseh

Time: 6:30–10:30 PM · bonfire & marshmallow roast 6:30 PM · fireworks 9 PM/dusk

A great free family night! Kids can roast marshmallows and make s'mores around the community bonfire, enjoy live music from Max Marshall and take part in interactive lawn games before finishing the evening with fireworks.

Location: SUNSET Amphitheatre, Leamington waterfront

Time: 7:30 PM (The S'Aints headline at 8 PM)

A Labour Day weekend concert at Leamington's waterfront amphitheatre. Geared toward the whole family — bring lawn chairs or blankets, enjoy the waterfront and grab food on site.

Location: Thiessen Orchards, Leamington

Time: 10 AM – 5:30 PM (open daily Sept. 10 – Nov. 1)

Fall has officially arrived! Opening Day kicks off apple-picking season, giving families a chance to get outside, explore the orchard and start their fall traditions. Bonus: the 50th Anniversary Celebration on Sept. 12 adds live entertainment, face painting and kids' activities from 10 AM–5:30 PM.

Location: Windsor (check organizer for venue)

Time: 6–11 PM · JBandRob 6–8 PM · Gnome Chimpsky 8–10 PM

One of the best kid-friendly night market options this month! Families can enjoy food, vendors and entertainment while kids check out glow-in-the-dark mini golf, cornhole and magician Ron Gudel.

Location: Central Park Athletics, Windsor

Time: 10 AM – 5 PM both days

THIS is one of the big ones for families! Children's Fest is designed around kids, with bouncy castles, inflatables, games, stage shows, favourite characters, colouring, interactive activities and kid-focused vendors. The 2026 lineup includes Evermore Princess Parties, Story Time with Al the Dinosaur, Youcan the Toucan, the 501st Garrison, Windsor Fire & Rescue and a soap box derby. Admission: $5/person (under 2 free); weekend pass $8.

Location: Participating farms across Windsor-Essex

Time: 9 AM – 5 PM

A fantastic option for families who want to get outside and learn where their food comes from. Farms, growers and producers open their doors for behind-the-scenes tours, tastings, hands-on activities and family-friendly farm experiences. FREE — families should register for the digital pass.

Location: Windsor/Essex County Humane Society

Time: 11 AM – 3 PM

A particularly good event for animal-loving kids! The Humane Society celebrates 100 years with a family open house featuring Bluey and Bingo, a doggie fashion show, Windsor Police K9 demonstration, local vendors, BBQ, special guests and family activities.

Location: Point Pelee National Park, Leamington

Time: 7:30 PM – midnight

A completely different kind of family adventure — explore Point Pelee after dark and experience its famously dark skies. A great opportunity for older kids to learn about astronomy and spot stars. Included with park admission.

Location: Cottam

Time: 9 AM – 4 PM · pancake breakfast 9 AM · parade noon · pony rides 1–4 PM · wrestling 2:30 PM

Another huge family pick — and FREE! Kids can enjoy free bouncy castles and inflatables all day, a petting zoo, pony rides, crafts, activities, a horse show, bird show and bunny races. There's also a parade at noon and wrestling at 2:30 PM.

Location: Downtown Amherstburg

Time: Schedule varies — 2026 details still being released

Steampunk meets wizardry! Kids can dress up, explore downtown, watch street performers, check out vendors and participate in games and interactive activities. The festival includes Wizard Academy, wizard bingo, button making, escape rooms, performances and plenty of cosplay photo opportunities.

Location: City Hall Square, Downtown Windsor

Time: 12–6 PM

A FREE family-friendly celebration of Windsor-style pizza! Kids can enjoy the lively atmosphere, pizza-themed experiences, demonstrations and entertainment while parents sample pizza from local restaurants.

Location: WFCU Centre, Windsor

Time: 7:05 PM

The Spitfires officially open their home season against the London Knights. A fun option for hockey-loving families — especially older kids who enjoy the energy of a live OHL game.

Location: Holiday Beach Conservation Area, Amherstburg

Time: 9 AM – 3 PM both days · $20 per vehicle/day

One of the coolest educational family events in the region! Watch thousands of hawks, eagles and falcons migrating overhead while enjoying live birds of prey demonstrations, guided hikes, presentations, exhibits and children's activities.

Location: Sauve's Country Market

Time: Time TBA

A laid-back fall market featuring local makers, crafts, treats and classic fall flavours from Sauve's Country Kitchen. More of a family browsing stop than a dedicated kids event, but it pairs nicely with a fall day out.

Location: Downtown Windsor

Time: 9 AM – 2 PM

Especially worth including for families thanks to its Kids Corner, along with crafts, art exhibits, community booths, entertainment and food demonstrations. Kids can browse while parents shop local produce, baked goods and handmade products.

Location: Colchester

Time: Time TBA

A smaller local market featuring vendors and unique finds. Good for families looking for a quieter community-market outing.

Location: Two routes across Windsor with seven community hubs

Time: 10 AM – 2 PM

FREE and VERY family-friendly. Windsor streets become car-free spaces where families can walk, bike, rollerblade and explore. Seven community hubs host interactive activities focused on health, arts, culture, heritage and community — kids can collect seven landmark-themed stickers by visiting the hubs.

Location: Windsor & Kingsville (check registration location)

Time: Kingsville: registration 9 AM · opening ceremony 10 AM · 2K & 5K start 10:30 AM

A great opportunity to get the whole family active while supporting cancer research. The run is non-competitive — participants can run, walk or ride at their own pace, and strollers and dogs are welcome at the Kingsville-area event.

Location: Lacasse Park, Tecumseh

Time: 9 AM – 1 PM

A great Sunday morning family stop with fresh produce, baked goods, handmade products and local vendors. A relaxed way to combine shopping local with a morning outdoors.

Location: Walkerville, Windsor

Time: 5–11 PM

A free, all-ages evening market with local makers, food trucks, pop-ups, live entertainment and outdoor games and activities. Kids are welcome, though the later hours make it best suited to families with older kids.

Location: Downtown Harrow

Time: 5–8 PM

Harrow's community street event brings local businesses, vendors and entertainment together for an evening where families can walk around and enjoy the downtown area. A nice small-town family night out.

Location: Ruthven

Time: 9 AM – 5 PM both days

A must-add fall family event! More than 100 craft and food vendors, a farmers market, live entertainment and plenty of fall atmosphere. Sunday also includes a car show.

Location: Capri Pizzeria Recreation Complex, Windsor

Time: 1–3 PM both days

Kids and families can try something completely different for FREE! Learn the basics of curling with equipment and instruction provided as part of Windsor's Staycation Activation.

Location: LaSalle

Time: 11 AM – 5 PM

More than 50 vendors, live demonstrations, competitions and health/fitness businesses come together in LaSalle. Geared more toward adults, but older kids and teens interested in sports and fitness could find something interesting. Free admission with registration.

Location: Windsor (check organizer for venue)

Time: Time TBA

A community gathering focused on education, remembrance and reconciliation — an important opportunity for families with older children to learn about Indigenous history and the meaning behind Truth and Reconciliation.

Location: Boonies Drive-In, Tilbury

Time: Gates 4 PM · Truck or Treat 6–7 PM · Hotel Transylvania 7:45 PM · The Addams Family to follow · rain date Sept. 27

A BIG one for kids! Dress up, decorate your vehicle and enjoy a Halloween-themed evening under the stars. Truck or Treat runs 6–7 PM where kids go vehicle-to-vehicle collecting candy, plus a truck decorating competition, vendors and a double-feature movie night. $35 per carload.

Location: Lakewood Park South, Tecumseh

Time: 11 AM – 3 PM

A free, family- and pet-friendly community market. Browse local vendors, handmade goods and treats while enjoying the park — a relaxed market that works well as part of a Sunday outing.