Another week, another packed lineup of events across Windsor-Essex.

Whether you're planning a family outing, date night, or weekend adventure, you'll find plenty to explore—from live concerts and theatre to comedy shows, festivals, farmers' markets, waterfront events, and unique local experiences.

July 9 – July 16

Here's what's happening around Windsor-Essex this week.

🎭 July 16–26 – Talley's Folly
Various Times | Christ Church Colchester

Experience Lanford Wilson's beloved romantic comedy, Talley's Folly, presented by Inspired Acting Lab in the charming setting of Christ Church Colchester. Follow the heartfelt story of Matt and Sally as they navigate love, family, and second chances in 1944.

Pair the performance with a visit to Colchester's wineries or restaurants for the perfect summer evening. 🍷✨

More Info

Windsor’s music scene is stacked this season—from techno nights and live summer DJ parties, there’s a sound for every vibe and every night out.

🎶 July 9 – Live at the Lighthouse
7:00 PM – 8:30 PM | Mettawas Park Gazebo
Enjoy a relaxing summer evening at Live at the Lighthouse, a free weekly concert series held beside the Kingsville Lighthouse. On July 9, Rick Stephenson – His Sinatra will perform a collection of Frank Sinatra classics and easy-listening favourites in a beautiful waterfront setting.

🎤 July 10 – 1999: The Ultimate Prince Experience
8:00 PM | Chrysler Theatre
Celebrate the legendary music of Prince with 1999: The Ultimate Prince Experience, an electrifying tribute concert starring Dale Ray and an exceptional eight-piece live band. This show combines powerful live performances, dazzling costumes, and stunning visuals to capture the energy, creativity, and unforgettable stage presence of one of music's greatest icons.

🎺 July 10 – FREE Summer Concert: Sculpture Garden
7:00 PM | Sculpture Garden, Windsor
Spend a relaxing summer evening by the waterfront with a free outdoor performance by the Windsor Symphony Orchestra Brass Quintet. This family-friendly event invites guests to bring a lawn chair, blanket, or picnic basket and enjoy an evening of live brass music in the beautiful Sculpture Garden.

🎼 July 10–12 – Windsor Symphony Orchestra Summer Concert Series
See Description | Various Locations
Enjoy the sounds of live orchestral music outdoors during the Windsor Symphony Orchestra Summer Concert Series.

🎶 July 10 – Music Off The Back Porch at Park House Museum
6:00 PM – 8:00 PM | Park House Museum
Spend a relaxing summer evening enjoying live music at the historic Park House Museum during the Music Off The Back Porch series.

🎤 July 11 – Taylor: A Tribute to the Eras of Taylor Swift
7:30 PM | Chrysler Theatre
Celebrate the music, storytelling, and unforgettable moments of Taylor Swift’s career at Taylor: A Tribute to the Eras of Taylor Swift. This spectacular tribute show brings each era to life with carefully recreated costumes, vocals, and performances that capture the spirit and emotion of Taylor’s biggest albums.

🎵 July 11 – Live Music at Parkside Grille
Evening | Rochester Place
Enjoy a memorable summer evening at Rochester Place with live music, delicious food, and scenic golf course views. Under the outdoor tented patio, guests can relax to a live performance by Chiq Quattro while enjoying rotating food truck-style menus, handcrafted cocktails, and refreshing summer beverages from the outdoor bar.

🎵 July 11–12 – Mystic Garden Music Festival
See Description | Lanspeary Park
Step into a vibrant world of music, art, and creativity at the Mystic Garden Music Festival, a two-day outdoor celebration of electronic music and community. Curated by Kenekted and NXT LVL Productions, the festival features an exciting lineup of electronic music artists, immersive art installations, live performances, local food vendors, handcrafted goods, and interactive experiences.

🎶 July 11 – Music Onthe42 Summer Concert Series: Mary Frances Leahy
7:30 PM | SUNSET® Amphitheatre, Seacliff Park
Spend a summer evening by the waterfront at Leamington’s Music Onthe42 Summer Concert Series. The night begins with a performance by Andrew MacLeod at 7:30 PM, followed by headliner Mary Frances Leahy at 8:30 PM.

🍷 July 11–12 – Uncorked Weekend
Pelee Island Winery, Kingsville
Spend a relaxing summer weekend at Pelee Island Winery with live jazz, award-winning wines, and authentic wood-fired Neapolitan pizza.

🎶 July 11 – Riverfront Rewind
4:00 PM – 9:00 PM | Reaume Park
Step back in time at Riverfront Rewind, a free waterfront celebration filled with live music, classic cars, retro games, local food and drinks, and nostalgic entertainment along the Detroit River.

🎧 July 11 – Electro on Erie
9:00 PM | Erie St GastroPub
Keep the weekend going with Electro on Erie, a lively night of electronic lounge music featuring resident DJ Greg Gnyp alongside a rotating lineup of guest DJs.

🎵 July 12 – Sprucewood Shores Summer Music Series Featuring Portofino
1:00 PM – 3:00 PM | Sprucewood Shores Estate Winery
Spend a relaxing Sunday afternoon by the shores of Lake Erie with live music from Portofino, Windsor’s newest party band.

🎶 July 12 – Sunday Sounds at Oxley Estate Winery
1:00 PM – 5:00 PM | Oxley Estate Winery
Unwind with an afternoon of live music, delicious food, and award-winning wines at Oxley Estate Winery’s popular Sunday Sounds series.

🎼 July 12 – Stone and Sky Music & Art Series
5:30 PM | The Quarry on Pelee Island
Experience an evening of live music and artistic expression at the Stone and Sky Music & Art Series on beautiful Pelee Island.

🎤 July 12 – Lord Huron at Caesars Windsor
7:30 PM | The Colosseum at Caesars Windsor
Acclaimed indie folk band Lord Huron takes the stage at Caesars Windsor for an unforgettable evening of atmospheric music and cinematic storytelling.

Windsor’s comedy scene is bringing nonstop laughs with stand-up showcases, lighting up intimate venues all across the city.

😂 July 11 – The Bridge: DETROIT Edition LIVE Comedy at Tipsy Toucan
8:00 PM | The Tipsy Toucan
Get ready for a night of big laughs as The Bridge: DETROIT Edition brings top Detroit comedian Josh Adams and two special guests across the border for an unforgettable evening of stand-up comedy.

🎭 July 10–11 – Cheer Up, Hamlet!
8:00 PM | Fogolar Furlan
Enjoy a hilarious outdoor theatrical experience with Cheer Up, Hamlet!, a playful Shakespeare-inspired comedy presented by A Palpable Hit Productions in partnership with Korda Artistic Productions and The Fogolar Furlan Club of Windsor.

😂 July 11 – Seth Meyers Live at Caesars Windsor
8:00 PM | The Colosseum at Caesars Windsor
Award-winning comedian, writer, and television host Seth Meyers brings his acclaimed stand-up comedy to The Colosseum at Caesars Windsor.

😂 July 14 – Phogheads Comedy Showcase
8:30 PM – 10:00 PM | Phog Lounge
Laugh your way through Tuesday night at the Phogheads Comedy Showcase, a free weekly stand-up comedy event featuring a rotating lineup of talented local and touring comedians.

🎉 July 9 – Hellenic Cultural Centre Grand Reopening Celebration
5:00 PM – 8:00 PM | Hellenic Cultural Centre
Celebrate the grand reopening of the newly renovated Hellenic Cultural Centre and experience its refreshed facilities, new management, and exciting rebrand. Guests can enjoy guided venue tours, wine tastings, complimentary appetizers, giveaways, and beautifully designed wedding and corporate event displays. The evening also marks the launch of the new Hellenic Table Catering To Go program.

🌞 July 10–12 – Amherstburg Open Air Weekends
Friday 3:00 PM – Sunday 8:00 PM | Downtown Amherstburg
Enjoy a fun-filled summer weekend in downtown Amherstburg with Amherstburg Open Air Weekends, a free community celebration featuring local shopping, delicious food, live entertainment, and activities for all ages. Browse the Friday evening local and youth market, explore unique boutiques and artisan vendors, and enjoy guided historic walking tours, yoga in the park, coffee and culture sessions, chess activities, and live performances throughout the weekend.

🎬 July 11 – City Cinema Saturdays
11:00 AM – 2:00 PM | SoCA Armouries Performance Hall
Kick off your weekend with a free family movie at City Cinema Saturdays, presented in partnership with the Windsor International Film Festival. On July 11, enjoy a screening of Shrek along with complimentary popcorn in a fun, family-friendly atmosphere. This summer movie series is the perfect way for families and friends to relax and enjoy a classic film together.

Enjoy markets, shows, fashion at Windsor.

🎨 July 9 – AWE Summer Nights
5:00 PM – 9:00 PM | Art Windsor Essex
Enjoy a relaxing summer evening at AWE Summer Nights, where art, food, and community come together in a beautiful waterfront setting.

🥁 July 10 – Seniors Drum Circle
See Description | African Village Africain Community Centre
Experience the healing power of rhythm at the Seniors Drum Circle, a wellness-focused program designed to promote connection, creativity, and cultural expression through African drumming.

🚗 July 10 – Belle River BIA Car Show
4:00 PM | Belle River BIA
Rev up for an exciting evening at the 23rd Annual Belle River BIA Car Show, where hundreds of classic cars, vintage vehicles, muscle cars, and hot rods line the streets of downtown Belle River.

🎨 July 10 – Mill St. Market: Eats, Beats & Art-filled Streets
5:00 PM – 10:00 PM | Mill Street, Leamington
Celebrate the rich culture and creativity of Leamington at the Mill St. Market: Eats, Beats & Art-filled Streets, a lively family-friendly street festival featuring live music, cultural performances, delicious international cuisine, handcrafted goods, locally grown products, craft beer, wine, and creative cocktails.de goods, delicious food, and live entertainment.

🐾 July 10 – Paw Patrol Meet & Greet: Chase, Marshall & Skye
11:00 AM – 3:00 PM | Devonshire Mall
Bring the family to Devonshire Mall for a fun-filled Paw Patrol Meet & Greet featuring Chase, Marshall, and Skye. Young fans will have the opportunity to meet their favourite rescue pups, snap memorable photos, and enjoy an exciting day of family entertainment.

🛍️ July 10 – Amherstburg Open Air Night Markets
Evening | Downtown Amherstburg
Spend a summer evening exploring the Amherstburg Open Air Night Markets, where live entertainment, local vendors, delicious food, and handmade treasures create a vibrant community atmosphere.

🎮 July 11–12 – Windsor-Essex FanCon (Summer 2026)
12:00 PM – 8:00 PM | LaSalle Event Centre
Celebrate all things geek, fandom, and pop culture at the Windsor-Essex FanCon, returning for its second annual event with two exciting days of entertainment and community. Explore Artist Alley, shop for collectibles and pop culture merchandise, compete or cheer on participants in the expanded cosplay contest, enjoy the gaming zone, and visit the family-friendly Kids Zone

🌽 July 11 – Downtown Windsor Farmers’ Market
See Description | Downtown Windsor
Discover the best of local food, handmade goods, and community spirit at the Downtown Windsor Farmers’ Market. Browse fresh seasonal fruits and vegetables, locally produced foods, artisan products, crafts, and unique handmade items from vendors across the region.

🎨 July 11–12 – Amherstburg Art Crawl
Downtown Amherstburg
Explore the vibrant arts scene during the Amherstburg Art Crawl, a weekend celebration of creativity throughout downtown Amherstburg.

🌸 July 11–12 – Kingsville Garden Tour, Tea and Flower Show
Self-Guided Tour | Kingsville
Discover the beauty of Kingsville’s finest private gardens during the Kingsville Garden Tour, Tea and Flower Show.

🛍️ July 11 – Lakeside Market
8:00 AM – 1:00 PM | Atlas Tube Centre
Spend your Saturday morning exploring the Lakeside Market, a vibrant community gathering featuring local farmers, growers, artisans, makers, food vendors, and small businesses.

🥕 July 11 – Downtown Windsor Farmers’ Market
9:00 AM – 2:00 PM | Pelissier Street
Discover the best of Windsor-Essex at the Downtown Windsor Farmers’ Market, featuring farm-fresh fruits and vegetables, artisan food products, local crafts, and handmade goods.

🌿 July 11 – Farmer’s Market in The Quarry
10:00 AM – 1:00 PM | Stone & Sky at The Quarry
Spend your Saturday morning at Stone & Sky’s weekly Farmers Market, featuring local vendors, fresh products, handmade goods, and a different live performer or artist each week.

🎮 July 11–12 – Windsor-Essex FanCon
Event Centre at LaSalle Landing
Celebrate all things geek, fandom, and pop culture at the second annual Windsor-Essex FanCon. This two-day event features cosplay competitions, artist alley, pop culture vendors, gaming experiences, special guests, panels, collectibles, and family-friendly activities.

🎪 July 11 – Not Another Pop-Up Market
12:00 PM – 5:00 PM | Walkerville Brewery
Discover a thoughtfully curated marketplace featuring talented local artists, handmade goods, vintage treasures, and original creative brands from across Windsor-Essex

🧺 July 12 – Sunday Farmers Market
11:00 AM – 2:00 PM | WindsorEats Food Hall
Spend your Sunday shopping local at the Sunday Farmers Market, where you can browse fresh produce, artisan products, and unique local vendors in a relaxed indoor setting.

🎭 July 12 – Rum Runners Tour
11:00 AM – 3:00 PM | Rockstar Music Hall
Step back into Windsor’s Prohibition era with the award-winning Rum Runners Tour, an immersive theatrical experience filled with colourful gangsters, rumrunners, live music, comedy, and historic storytelling.

🎨 July 12 – Weekends in the Studio: By the Pool Watercolours with Suela Prendi
1:00 PM – 4:00 PM | Art Windsor Essex
Discover the art of watercolour painting in this free drop-in workshop led by artist Suela Prendi. Participants will create a vibrant poolside scene while learning techniques such as colour glazing, wet-on-wet washes, and wet-on-dry detailing

🎨 July 15 – Mandala Journal Painting Workshop
6:00 PM – 8:00 PM | The Beerded Dog Brewing Company
Unwind with a relaxing evening of creativity at this Mandala Journal Painting Workshop, where participants will design a personalized journal cover and matching bookmark using acrylic paints and mandala dot-painting techniques.

Enjoy games, trivia and dinner nights in Windsor.

🎯 July 10 – Royal Canadian Legion Branch #644 Luck of the Draw Friday Dart Night
7:30 PM | Royal Canadian Legion Branch #644
Test your aim and enjoy a fun evening of friendly competition at the Royal Canadian Legion Branch #644's weekly Luck of the Draw Dart Night.

🛳️ July 10 – Swifty Night Cruise
6:00 PM – 10:00 PM | Windsor Premier Cruises
Swifties are invited aboard the Macassa Bay for an unforgettable evening celebrating the music of Taylor Swift. Dance the night away as DJ Niko Jay spins Taylor’s biggest hits while special guest Lauren Victoria sets the mood during boarding.

🍽️ July 10 – Terrace Dinners: Greece
Evening | St. Clair College Centre for the Arts
Experience an unforgettable rooftop dining evening overlooking the Detroit skyline at the St. Clair College Centre for the Arts.

🎬 July 10 – Moonlight Movie Night
8:30 PM | Tecumseh Town Centre Park
Enjoy a relaxing summer evening with a free outdoor movie under the stars at Tecumseh Town Centre Park.

🎬 July 11 – The Boonies: Drive-In Movie Night
See Description | The Boonies Drive-In Theatre
Experience the nostalgia of classic outdoor cinema at The Boonies Drive-In Movie Night. Pack the car, bring your blankets and lawn chairs, and enjoy a memorable evening watching movies under the stars with family and friends.

🛳️ July 11 – Y2K Cruise
7:00 PM – 11:00 PM | Windsor Premier Cruises
Throw it back to the early 2000s aboard the Macassa Bay with the Y2K Cruise. Dance the night away as DJ Niko spins the biggest pop, hip-hop, R&B, electronic, and rock hits from the millennium era while enjoying stunning views of the Windsor and Detroit waterfront.

🎵 July 12 – Music Bingo Trivia at Walkerville Brewery
5:00 PM – 7:00 PM | Walkerville Brewery
Test your music knowledge at Music Bingo Trivia, a fun evening that combines bingo, trivia, and great music with host Mack Flash Entertainment.

🌅 July 16 – Dinner & Sunset Cruise
6:00 PM | St. Clair College Centre for the Arts & Windsor Premier Cruises
Enjoy an unforgettable summer evening beginning with a delicious three-course plated dinner on the rooftop Viewpoint Terrace at the St. Clair College Centre for the Arts.

⛸️ July 10 – PLAY FOR FREE! WFCU Centre Free Skating
2:40 PM – 4:40 PM | WFCU Centre
Enjoy a fun afternoon on the ice with free public skating at the WFCU Centre as part of Windsor’s Staycation Activation program.

🛼 July 10 – Wheels Nights at City Hall Square
6:00 PM – 10:00 PM | City Hall Square
Roll into a nostalgic summer evening at Wheels Nights, a free outdoor roller-skating experience inspired by Windsor’s iconic Wheels! roller rink. As part of the Staycation Activation program, City Hall Square transforms into a lively roller rink featuring music, DJs, colourful lighting, themed entertainment, costumes, and roller skate rentals.

🥊 July 12 – Rising Stars Fight Series 5: Night of Champions
2:30 PM – 7:00 PM | Capri Pizzeria Recreation Complex
Experience an action-packed afternoon of combat sports at Rising Stars Fight Series 5: Night of Champions, featuring both MMA and kickboxing inside the same cage.

♟️ July 14 – Chapter Two Brewing Company Chess Club
| Chapter Two Brewing Company
Enjoy a relaxed evening of chess, craft beer, and friendly competition at the Chapter Two Brewing Company Chess Club.

⚽ July 15 – FIFA World Cup 2026™ Canada Celebrates
12:00 PM – 8:00 PM | City Hall Square, Charles Clarke Square & University Avenue
Celebrate the excitement of the FIFA World Cup 2026™ as communities across Canada come together for this free, family-friendly festival in downtown Windsor.