Summer is heating up across Windsor-Essex, and the region is packed with major festivals, live entertainment, cultural celebrations, and Canada Day festivities.

From downtown parades and waterfront concerts to large-scale festivals just outside the city, there’s no shortage of ways to get out and enjoy the week ahead.

June 25 – July 2

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

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 10 – 1999: The Ultimate Prince Experience
8:00 PM | Chrysler Theatre

Celebrate the music of Prince with a spectacular tribute featuring Dale Ray and an 8-piece live band. Enjoy iconic hits, stunning costumes, and an electrifying performance that captures the energy, style, and legacy of one of music’s greatest innovators. 💜🎤

🎤 July 11 – Taylor: A Tribute to the Eras
7:30 PM | Chrysler Theatre

A high-energy tribute to Taylor Swift featuring Josette, live band, and dancers. Experience over 20 hit songs from every era—including Love Story, Shake It Off, Anti-Hero, and Blank Space—in a sparkling, full-scale concert-style production celebrating her biggest moments. 🎶✨

🎻 June 25 – Great Lakes Chamber Music Festival 2026: Rhythms of Place
7:00 PM – 8:30 PM | Capitol Theatre
Experience an inspiring evening of chamber music at Rhythms of Place, presented as part of the Great Lakes Chamber Music Festival 2026. This elegant concert explores the connection between classical traditions and folk-inspired rhythms.

🎤 June 27 – Jordan Davis Takes Centre Stage in The Colosseum
8:00 PM | The Colosseum at Caesars Windsor
Country music fans won't want to miss Multi-Platinum, award-winning singer-songwriter Jordan Davis live in concert at The Colosseum.

🎧 June 27 – Electro on Erie
9:00 PM – Late | Erie St GastroPub
Experience a night of electronic music and vibrant nightlife at Electro on Erie. Featuring resident DJ Greg Gnyp along with a rotating lineup of guest DJs each week, this late-night event delivers a mix of electro and lounge beats in a lively atmosphere

🎶 June 28 – Sprucewood Shores Summer Music Series Featuring Buck Twenty
1:00 PM – 3:00 PM | Sprucewood Shores Estate Winery
Spend a relaxing afternoon by Lake Erie with live music, local wine, and beautiful waterfront views at the Sprucewood Shores Summer Music Series.

🎵 June 28 – Sunday Sounds at Oxley Estate Winery
1:00 PM – 5:00 PM | Oxley Estate Winery
Enjoy an afternoon of live music, award-winning wine, delicious food, and scenic vineyard views at Sunday Sounds at Oxley Estate Winery.

🎭 June 28 – ENCORE
4:00 PM | Rockstar Music Hall
Enjoy an elegant evening of live entertainment, music, dance, and dining at ENCORE, a spectacular stage production celebrating some of the most memorable performances from theatre, film, and live entertainment. F

🎷 June 28 – Jazz Night Brewery
6:00 PM – 9:00 PM | Walkerville Brewery
Unwind with an evening of smooth live jazz at Walkerville Brewery’s monthly Jazz Night. Held on the last Sunday of each month, this popular event features live performances by The Coffee House Combo, delivering a relaxing mix of classic jazz and contemporary favorites.

🎸 July 1 – Leamington’s Music Onthe42 Summer Concert Series: Big Shiny Toons – Ultimate Tribute to the 90s
7:30 PM | SUNSET® Amphitheatre, Seacliff Park
Kick off Canada Day celebrations with an evening of free live music at Leamington’s Music Onthe42 Summer Concert Series.

🎷 July 2 – Live at the Lighthouse Featuring 401 Smooth Jazz
7:00 PM – 8:30 PM | Mettawas Park Gazebo
Enjoy a relaxing summer evening by the waterfront at Kingsville’s Live at the Lighthouse concert series. Kicking off the July lineup is 401 Smooth Jazz, bringing a blend of smooth jazz, Latin rhythms, and instrumental pop music to the scenic gazebo beside the Kingsville Lighthouse.

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

😂 June 25 – Mike Cannon LIVE Comedy at Tipsy Toucan
8:00 PM | The Tipsy Toucan
Get ready for a night of sharp, high-energy stand-up comedy as New York City comedian Mike Cannon takes the stage at The Tipsy Toucan. Known for his quick wit, relatable storytelling, and fearless sense of humor, Cannon has performed at some of the world’s most iconic comedy venues and regularly appears at leg

😂 June 25 – Daniel Tosh: My First Farewell Tour
8:00 PM | The Colosseum at Caesars Windsor
Comedy fans won't want to miss Daniel Tosh as he brings his My First Farewell Tour to Caesars Windsor for one night only.

😂 June 27 – Keesha Brownie LIVE Comedy at Tipsy Toucan
8:00 PM – 9:30 PM | The Tipsy Toucan
Enjoy an evening of laughter with acclaimed Canadian comedian Keesha Brownie at Windsor’s premier live comedy venue. Keesha combines her background in theatre, sketch comedy, and music to deliver a unique comedic style inspired by her Jamaican heritage and Canadian upbringing

🏳️‍🌈 June 26–28 – Amherstburg Open Air Weekends: PRIDE Weekend
See Description | Downtown Amherstburg
Celebrate Pride in downtown Amherstburg during this vibrant Open Air Weekend. Enjoy live entertainment, dance parties, and fun Pride-themed activities. Explore local shops, cafés, restaurants, and vendors throughout the event.

🪶 June 26 – Indigenous History Month Celebration Competition Powwow
12:00 PM – 9:00 PM | Charles Clark Square
Celebrate Indigenous History Month at the 2026 Competition Powwow in Charles Clark Square. Experience traditional drumming, singing, and competitive dance performances while learning about and celebrating Indigenous cultures. Connect with the community through a day of heritage, tradition, and cultural sharing.

🌶️June 26–27 – Windsor Jerk Fest
See Description | Windsor Essex Caribbean Association – Caribbean Centre
Experience the flavours, music, and culture of the Caribbean at the third annual Windsor Jerk Fest. Enjoy authentic jerk cuisine, cultural performances, and live entertainment in a lively festival atmosphere. Featuring Jamaican artist Louie Culture and Detroit’s Universal Expression.

🏳️‍🌈 June 27–28 – TRUE Fest Exhibit
10:00 AM – 4:00 PM | Park House Museum
Celebrate diversity, history, and community at the TRUE Fest Exhibit at the Park House Museum. Explore the We Were Always Here exhibit honoring 2SLGBTQ+ history and contributions. Enjoy crafts, activities, and a community picnic in a welcoming space focused on inclusion and cultural awareness.

💜 June 27–28 – Lavender Festival
See Description | North 42 Degrees Estate Winery
Celebrate lavender season at North 42 Degrees Estate Winery during a weekend of art, music, food, and wine. Browse artisans, enjoy live performances, and relax among blooming lavender fields. Don’t miss the winery’s signature lavender lemonade slushies and family-friendly activities.

Enjoy markets, shows, fashion at Windsor.

🎭 June 25-26 – 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 – Windsor Riverfront Carnival
12:00 PM (Weekends) | 4:00 PM (Weekdays) | Windsor Riverfront
Kick off the summer season at the Windsor Riverfront Carnival, a beloved annual tradition along the city's scenic waterfront. This family-friendly event features exciting midway rides, classic carnival games, and a lively atmosphere for visitors of all ages.

🎭 June 25 – An Echo of the Soul: Tchaikovsky and His Women
7:30 PM | The Shadowbox Theatre
Experience a captivating theatrical journey into the life of renowned Russian composer Pyotr Ilyich Tchaikovsky in An Echo of the Soul: Tchaikovsky and His Women. Blending history, music, and emotion, the production offers an intimate look at the personal struggles, inspirations, and artistic brilliance.

🎭 June 25–26 – Greedy Gallery Gals
7:00 PM | Sho Art, Spirit & Performance
Step into a world of secrets, deception, and hilarious mishaps with Greedy Gallery Gals, a fast-paced comedy about three women who join forces to steal a painting worth $3 million. Their carefully crafted plan quickly begins to unravel as suspicion, unexpected twists, and chaos take over.

🌳 June 25 – Neighbourhood Nights: Optimist Memorial Park
6:30 PM – 9:00 PM | Optimist Memorial Park
Join your neighbours for an evening of community spirit, entertainment, and family-friendly fun at Neighbourhood Nights.

🥁 June 26 – Seniors Drum Circle
See Description | African Village Africain Community Centre
Join the Seniors Drum Circle, a culturally enriching and wellness-focused program designed to promote connection, creativity, and well-being among older adults.

🎪 June 26–28 – The Great Benjamins Circus
See Description | Leamington District Agricultural Society
Step right up for an unforgettable family experience as The Great Benjamins Circus brings its all-new 2026 show to Leamington.

🌙 June 26 – Amherstburg Open Air Night Markets
Evening Hours | Downtown Amherstburg
Experience the charm of downtown Amherstburg after dark at the Amherstburg Open Air Night Markets. Held every Friday evening throughout the summer, this vibrant community event brings together local vendors, artisans, food vendors, and live entertainment in a welcoming outdoor setting.

🏴 June 26 – Banded Goose Brewing Co. Highland Games Ceilidh
3:00 PM | Banded Goose Brewing Co.
Celebrate Scottish culture and community at the Highland Games Ceilidh at Banded Goose Brewing Co. As part of the Kingsville Highland Games festivities, this gathering brings the spirit of the Highlands to the shores of Lake Erie with an afternoon of tradition, hospitality, and celebration.

🚶 June 26 – Harrow Open Streets
5:00 PM – 8:00 PM | Downtown Harrow
Spend a summer evening exploring downtown Harrow during Harrow Open Streets, a lively community event filled with shopping, entertainment, and family-friendly fun.

🏴 June 27 – Kingsville Highland Games
See Description | Colasanti’s Tropical Gardens
Experience the sights, sounds, and traditions of Scotland at the Kingsville Highland Games, where the spirit of the Highlands meets the shores of Lake Erie.

💃 June 27 – Ladies Day Out
See Description | Wineology
Gather your friends and enjoy an uplifting day designed exclusively for women at Ladies Day Out. Hosted by Shexists, this girls-only event creates a welcoming space for women to connect, relax, celebrate, and enjoy a day filled with positive energy.

🧘 June 27 – Pints & Pilates
See Description | Billys Taphouse
Start your day with a refreshing combination of fitness and relaxation at Pints & Pilates. This unique outdoor event features an energizing Mat Pilates class held on the grass, offering participants the chance to strengthen their core, improve flexibility, and enjoy movement in a relaxed open-air setting.

🏄 June 27–28 – Adventure Bay Family Water Park: FlowRider is Back in Action
See Description | Adventure Bay Family Water Park
Get ready to ride the waves as the FlowRider returns to Adventure Bay Family Water Park. This exciting bodyboarding attraction uses powerful jet-propelled water to create a continuous wave experience, giving guests the thrill of surfing right in Windsor

🛍️ June 27 – Lakeside Market Grand Opening
8:00 AM – 1:00 PM | Atlas Tube Centre
Presented by Lakeside Home Solutions, the Lakeside Market brings together local farmers, growers, makers, artisans, small businesses, food vendors, and community organizations in a vibrant marketplace celebrating local talent and the bounty of the region

🌽 June 27 – Downtown Windsor Farmers’ Market
9:00 AM – 2:00 PM | Pelissier Street (between Wyandotte & Park)
Discover the best of local agriculture, artisan foods, and community spirit at the Downtown Windsor Farmers’ Market.

🌷 June 27–28 – Amherstburg Horticultural Society Garden Tour 2026
See Description | Toddy Jones Park
Explore some of Amherstburg’s most beautiful private gardens during the Amherstburg Horticultural Society Garden Tour 2026.

☀️ June 27 – Windsor-Essex Taste of Summer Market
11:00 AM – 5:00 PM | WFCU Centre
Celebrate the season at the Windsor-Essex Taste of Summer Market, a vibrant community event showcasing the best of local businesses and makers

🎆 June 27 – Pelee Island Fireworks
9:45 PM | Pelee Island Ferry Dock (West Side)
Celebrate a summer evening on Pelee Island with the return of the island’s annual fireworks display. Beginning at approximately 9:45 PM, the skies above the West Side ferry dock will come alive with a spectacular showcase of colourful fireworks

🌙 June 28 – LaSalle Night Markets
4:00 PM – 8:00 PM | LaSalle Civic Centre
Experience an evening of local shopping, food, and community at the LaSalle Night Markets. This vibrant market brings together talented artisans, crafters, local businesses, farm-to-table producers, food vendors, and merchant consultants, offering a wide variety of handmade and handcrafted products.

Enjoy games, trivia and dinner nights in Windsor.

🎲 June 25 – Brews & Board Games at Walkerville Brewery
5:00 PM | Walkerville Brewery
Gather your friends for an evening of games, great conversation, and local craft beer at Brews & Board Games, hosted by Tabletop Bellhop.

🎯 June 26 – Royal Canadian Legion Br. 644 Luck of the Draw Friday Dart Night
7:30 PM | Royal Canadian Legion Branch #644
Join fellow dart enthusiasts for Luck of the Draw Friday Dart Night at Royal Canadian Legion Branch #644. Open to players of all skill levels, this weekly event offers a fun and welcoming environment where participants can enjoy friendly competitions.

🍝 June 26 – Giro d’Italia Regional Dinner
6:00 PM | Giovanni Caboto Club
Celebrate Italian Heritage Month with an elegant evening of authentic regional Italian cuisine, live entertainment, and warm hospitality at the Giro d’Italia Regional Dinner. Following dinner, guests can enjoy live music and dancing with the Portofino Band, creating a festive atmosphere that celebrates Italian culture, food, and community.

🌙 June 26 – Walkerville Distillery District Night Market
5:00 PM – 11:00 PM | Walkerville Brewery
Experience one of Windsor’s most popular summer community events at the Walkerville Distillery District Night Market. This vibrant outdoor market celebrates local art, food, entertainment, and small businesses in the heart of the historic Walkerville district.

🎶 June 27–28 – Erie Street GastroPub Block Party
See Description | Erie St GastroPub
Enjoy a weekend of live music, great food, refreshing drinks, and outdoor summer fun at the Erie Street GastroPub Block Party. Part of a seasonal series of celebrations, this lively festival transforms the area around Erie St GastroPub into a vibrant gathering space featuring extended patios.

🎉 June 27 – Throwback Prom
7:00 PM | St. Clair Centre for the Arts
Step back in time and relive the magic of prom at Throwback Prom, a nostalgic evening where guests are encouraged to dress in their favorite fashion from any era.

🌕 June 29 – Howl at the Moon Dinner Series
5:00 PM – 8:00 PM | Oxley Estate Winery
Experience a memorable evening under the full moon at Oxley Estate Winery’s popular Howl at the Moon Dinner Series. Set in the heart of Essex County wine country, this special event combines exceptional dining, award-winning wines, and live music in a picturesque vineyard setting.

🃏 June 28 – CardCon: The Ultimate Windsor Card Show
10:00 AM – 5:00 PM | Giovanni Caboto Club
Calling all collectors and hobby enthusiasts! CardCon brings together sports card collectors, trading card fans, memorabilia hunters, and collectible enthusiasts for a full day dedicated to the hobby.