Summer is in full swing across Windsor-Essex, and the calendar is packed with reasons to get out and explore.

From live music and theatre to festivals, markets, sports, and community events, there’s something happening in every corner of the region this week.

June 18 – June 25

Here’s what’s worth checking out around Windsor this week.

🎨 June 24 – Paint Your Match Speed Dating
6:30 PM | 1009 Drouillard Rd Unit 2

A unique speed dating experience where singles paint each other's portraits while rotating between dates. Enjoy creative conversations, fun icebreakers, and post-event mingling designed to spark genuine connections. 💕🎨

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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 4 – Best of the Bee Gees & Rod Stewart
7:30 PM | Capitol Theatre

Experience an unforgettable night of classic hits as Night Fever, the acclaimed Bee Gees tribute show, joins forces with Forever Young, a dynamic tribute to Rod Stewart. Featuring an all-Canadian cast, this benefit concert supports Make-A-Wish Canada and delivers a nostalgic evening filled with timeless songs, energy, and entertainment. ✨

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🎵 June 18 – Sarah Smith Summer Tour 2026
8:00 PM | The Man’s Shop & Barbershop Bar
Join Sarah Smith for an energetic evening of live music, dancing, and crowd-favourite songs as part of her Summer Tour 2026. Sarah delivers a fun-filled concert experience that encourages audiences to sing along and enjoy a night of great entertainment.

🎹 June 18 – Dueling Pianos at Walkerville Brewery
7:00 PM | Walkerville Brewery
Join Rose City Dueling Pianos featuring Mark Calcott and Frankie Turner for an evening of live music, laughter, and audience interaction. Get ready to sing along, make song requests, and enjoy a unique performance as two talented pianists go head-to-head on the keys.

🎷 June 19 – Jazz Cats Concert
7:30 PM | Canadian Aviation Museum
Enjoy an unforgettable evening of live jazz music as the Jazz Cats take the stage in support of the Canadian Aviation Museum. This special fundraising concert brings together great music, community spirit, and a shared passion for preserving aviation history.

🎬 June 19 – School of Rock Movie Night
7:00 PM | Chrysler Theatre
Enjoy a special screening of the beloved comedy School of Rock starring Jack Black. This entertaining film follows struggling guitarist Dewey Finn, who poses as a substitute teacher at a prestigious prep school and discovers the musical talents of his students.

🎤 June 19 – Jann Arden Live
8:00 PM | Caesars Windsor
Award-winning Canadian singer-songwriter Jann Arden takes the stage for an unforgettable evening of music and storytelling at Caesars Windsor. Arden has captivated audiences for decades with beloved hits and personal reflections that blend humor, honesty, and emotion.

🎶 June 19 – Music Off The Back Porch at the Park House Museum
6:00 PM – 8:00 PM | Park House Museum
Enjoy a relaxing evening of live music in the charming historic setting of the Park House Museum. Music Off The Back Porch brings the community together for an intimate outdoor concert experience where visitors can unwind, appreciate local talent, and soak in the unique atmosphere of one of Amherstburg’s treasured heritage sites.

🎸 June 20 – UK PINK FLOYD: A Tribute to the Floyd
7:30 PM | The Chrysler Theatre
Experience the music and magic of Pink Floyd with UK PINK FLOYD’s acclaimed “The Songs from Every Album Tour.” Featuring selections from all 15 of Pink Floyd’s studio albums, this spectacular tribute concert delivers extraordinary musical accuracy and an immersive light show that captures the essence of one of rock’s most influential bands.

🎧 June 20 – Electro on Erie
9:00 PM | Erie St GastroPub
Enjoy an evening of electronic lounge music and vibrant nightlife at Electro on Erie. Featuring resident DJ Greg Gnyp alongside a rotating lineup of guest DJs, this weekly event delivers smooth beats, energetic rhythms, and a welcoming atmosphere perfect for a night out with friends.

🎶 June 21 – Sunday Sounds at Oxley Estate Winery
1:00 PM – 5:00 PM | Oxley Estate Winery
Spend a relaxing Sunday afternoon at Oxley Estate Winery with live music, great food, and award-winning wines in a beautiful vineyard setting

🎸 June 21 – Summer Sundays with Cherry Rock Lounge & 89X
7:30 PM – 10:00 PM | Cherry Rock Lounge
Keep the weekend going with Summer Sundays at Cherry Rock Lounge in partnership with 89X. This lively weekly event brings together great music, refreshing drinks, and a fun social atmosphere to help you end the weekend on a high note.

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

😂 June 19 – Standup at Sidelines! Featuring Dads!
8:00 PM | Sidelines Sports Bar & Grill
Celebrate Father’s Day weekend with an evening of comedy, stories, and plenty of laughs at Sidelines Sports Bar & Grill. Expect witty observations, classic dad jokes, and relatable stories that will have audiences laughing all night long. Grab a bite, enjoy a drink, and join friends for a fun-filled pre–Father’s Day comedy event.

😂 June 20 – Jason Allen LIVE Comedy at Tipsy Toucan
8:00 PM | The Tipsy Toucan
Enjoy a night of stand-up comedy with Canadian comedian Jason Allen, known for his honest, rapid-fire style and performances across North America.

😂 June 20 – Desi AF Featuring: Sonya Vai
7:00 PM | Meteor
Prepare for an unforgettable night of stand-up comedy as New York City comedian Sonya Vai brings her bold, fearless, and culturally charged humor to Windsor. Sonya tackles topics ranging from immigrant experiences and family dynamics to dating mishaps and everyday chaos.

😂 June 25 – Mike Cannon LIVE Comedy at Tipsy Toucan
8:00 PM | The Tipsy Toucan
Enjoy an evening of top-tier stand-up comedy with New York City comedian Mike Cannon. A comedian, podcaster, writer, and actor, Cannon has headlined renowned venues across North America and is known for his sharp observations, quick wit, and engaging storytelling

😂 June 25 – Daniel Tosh: My First Farewell Tour
8:00 PM | The Colosseum at Caesars Windsor
Get ready for a night of nonstop laughter as acclaimed comedian Daniel Tosh brings his My First Farewell Tour to The Colosseum at Caesars Windsor. Known for his sharp wit, fearless humor, and unique comedic style, Tosh rose to international fame as the creator and host of the long-running hit television series Tosh.0.

💃 June 19 – Windsor Dance eXperience: Strings: A Marionette’s Tale
See Description | Capitol Theatre Windsor
Experience an enchanting dance theatre production that tells the story of a magical doll who develops a soul and the courageous young hero determined to set her free. Controlled by a fearful Wizard who commands seven enchanted dolls, the special marionette inspires a journey of bravery, friendship, and hope as an entire town rallies behind her rescue. Through a captivating blend of jazz, ballet, and contemporary dance, this imaginative performance brings the story to life with over 60 talented dancers aged 8–14.

🍖 June 19–21 – Amherstburg Ribfest
11:00 AM | Ramsay Street, Amherstburg
Ribfest returns to Amherstburg for a delicious Father’s Day weekend celebration filled with mouthwatering barbecue, live entertainment, and family-friendly fun. Visitors can enjoy a variety of ribs and barbecue specialties prepared by talented vendors while taking in the lively festival atmosphere. This free-admission event offers something for everyone, making it a perfect destination for families, food lovers, and anyone looking to enjoy a summer weekend in downtown Amherstburg.

🎉 June 19–21 – Amherstburg Open Air Weekends: Rib Fest Weekend
3:00 PM Friday – 8:00 PM Sunday | Downtown Amherstburg
Experience a vibrant weekend in the heart of Amherstburg during Open Air Weekends. This free community event transforms downtown into a lively destination filled with local vendors, unique shopping, delicious food and drinks, live entertainment, and family-friendly activities. Visitors can enjoy guided historic walking tours, yoga in the park, coffee and culture sessions, chess activities, and performances by local artists throughout the weekend.

Enjoy markets, shows, fashion at Windsor.

🎭 June 18 – Ride the Cyclone
8:00 PM | Kordazone Theatre
Kordazone Theatre presents Ride the Cyclone, the acclaimed dark comedy musical by Jacob Richmond and Brooke Maxwell. In this hilarious and outlandish story, the lives of six teenagers from a Canadian chamber choir are cut short in a freak roller-coaster accident.

🎡 June 12–28 – Riverfront Midway
12:00 PM (Weekends) | 4:00 PM (Weekdays) | Windsor Riverfront
Kick off the summer at the annual Riverfront Midway, one of Windsor’s most popular seasonal attractions. Running from June 12 to June 28, the midway offers exciting rides, entertaining games, and family-friendly fun along the scenic waterfront.

🎭 June 19 – An Echo of the Soul: Tchaikovsky and His Women
7:30 PM | The Shadowbox Theatre
Experience a captivating theatrical drama exploring the life of renowned Russian composer Pyotr Ilyich Tchaikovsky and the two women who profoundly influenced his life during the period in which he composed his celebrated Fourth Symphony.

🥁 June 19 – Seniors Drum Circle
African Village Africain Community Centre
Join the Seniors Drum Circle, a culturally enriching wellness program designed to promote connection, creativity, and well-being among older adults.

🧺June 20 – Downtown Windsor Farmers’ Market
Downtown Windsor
Discover the best of local agriculture, food, and artisan craftsmanship at the Downtown Windsor Farmers’ Market. Visitors can browse a wide selection of farm-fresh fruits, vegetables, produce, baked goods, and unique artisan food products sourced from across the region.

🎡 June 12–28 – Windsor Riverfront Carnival
12:00 PM (Weekends) | 4:00 PM (Weekdays) | Windsor Riverfront
Celebrate the start of summer at the Windsor Riverfront Carnival, a long-standing seasonal tradition that brings excitement and family-friendly entertainment to the waterfront.

👨‍👩‍👧‍👦 June 20 – Family Father’s Day Charity Extravaganza
10:00 AM | St. Clair College SportsPlex
Celebrate Father’s Day weekend at Windsor-Essex’s largest free family event. The 8th Annual Family Father’s Day Charity Extravaganza offers a full day of entertainment, activities, and attractions designed for families with children aged 12 and unde

🧺 June 20 – Farmer’s Market in the Quarry
10:00 AM – 1:00 PM | Stone & Sky at The Quarry
Spend a relaxing morning at the Farmer’s Market in the Quarry, hosted weekly by Stone & Sky on beautiful Pelee Island. This family-friendly market features local vendors offering fresh produce, handmade goods, artisan products, and other unique items from the region

🛍️ June 20 – Colchester Markets
10:00 AM – 3:00 PM | Colchester Historic District
Experience a vibrant celebration of local culture, creativity, and community at the Colchester Markets.

🌍 June 19–21 – Carrousel of the Nations: Weekend Two
See Description | Various Locations
Experience one of Windsor-Essex’s most celebrated cultural festivals during Carrousel of the Nations. Recognized as one of Ontario’s premier festivals, this long-running event showcases the rich diversity of the region through a vibrant collection of cultural villages located throughout Windsor and Essex County.

🌽 June 21 – Tecumseh Farmers Market
9:00 AM – 1:00 PM | Lacasse Park
Discover the best of local agriculture, artisan products, and handmade goods at the Tecumseh Farmers Market. This community-focused market brings together talented local vendors offering fresh produce, baked goods, handcrafted items, specialty foods, and unique treasures from across the region.

🎨 June 23 – Terracotta Planter Pot Dot-Painting Workshop
6:00 PM – 8:00 PM | Banded Goose Brewing Co.
Unleash your creativity at this fun and relaxing Terracotta Planter Pot Dot-Painting Workshop. Participants will decorate their own terracotta planter using colourful dot-painting techniques and receive step-by-step guidance throughout the session

Enjoy games, trivia and dinner nights in Windsor.

🎯 June 19 – Luck of the Draw Friday Dart Night
7:30 PM | Royal Canadian Legion Branch #644
Join the weekly Luck of the Draw Dart Night for an evening of friendly competition and community fun. Open to players of all skill levels, this event welcomes both experienced dart enthusiasts and newcomers looking to enjoy the game

🍷 June 19–20 – Taste of Tecumseh
5:00 PM | Lakewood Park
Experience one of the region’s premier food and beverage festivals at Taste of Tecumseh. Set along the beautiful waterfront at Lakewood Park, this popular event brings together culinary delights, award-winning wines, craft beers, and live entertainment for an unforgettable summer celebration.

🎧 June 20 – Techno BLOCK PARTY
4:00 PM – 11:00 PM | Maiden Lane Art Alley
Experience an electrifying evening of music, art, and community at the Techno BLOCK PARTY in downtown Windsor. This free outdoor event transforms Art Alley into a vibrant celebration of techno culture.

☀️ June 20 – Kingsville Block Party: Summer Solstice – Cottam
5:00 PM – 10:00 PM | Cottam Centre
Celebrate the arrival of summer at the Kingsville Block Party in Cottam. This family-friendly community event brings together friends, neighbours, local businesses, and visitors for an evening of food, entertainment, shopping, and fun.

🎵 June 21 – Music Bingo Trivia at Walkerville Brewery
5:00 PM – 7:00 PM | Walkerville Brewery
Enjoy an entertaining evening of music, trivia, and friendly competition at Music Bingo Trivia hosted by Mack Flash Entertainment. This unique event combines the excitement of bingo with music knowledge and trivia challenges,

♟️ June 23 – Chapter Two Brewing Company Chess Club
See Description | Chapter Two Brewing Company
Enjoy an evening of strategy, socializing, and friendly competition at the Chapter Two Brewing Company Chess Club.

🏀 June 20 – Parents & Kids Basketball Camp
4:00 PM | WFCU Centre Sports Gym
Join the Windsor Express for a fun and interactive Parents & Kids Basketball Camp designed for youth ages 5–13 of all skill levels. Participants will have the opportunity to learn from Windsor Express coaches and players through engaging skills training, drills, and basketball activities.

⚽ June 18–19 – Community Soccer Watch Party at City Hall Square
3:00 PM – 8:00 PM | City Hall Square
Join fellow soccer fans for a two-day community celebration of international soccer at Windsor’s City Hall Square. This family-friendly event features live broadcasts of exciting international matches, families, and visitors together to enjoy the thrill of the game in a vibrant outdoor setting.

🤼 June 20 – NCG Live Pro Wrestling Presents: The Headbangers Ball
7:00 PM | Event Centre at LaSalle Landing
Experience an action-packed night of professional wrestling as NCG Pro Wrestling presents The Headbangers Ball.

That’s your Windsor-Essex week at a glance.

Whether you're exploring Carrousel of the Nations, enjoying a concert, browsing local markets, or spending time outdoors with family and friends, there’s no shortage of ways to make the most of the week.

Enjoy everything the region has to offer, support local events, and we’ll be back next week with more happening around Windsor-Essex.

— Windsor Pulse