Summer in Windsor-Essex is in full swing.

From live concerts and cultural festivals to bustling markets, rooftop dinners, and one-of-a-kind summer experiences, there's something for everyone across the region this week.

August 13 – August 20

Here's your guide to the best events happening around Windsor-Essex.

🛍️ August 15 – Colchester Markets
10:00 AM – 3:00 PM | Heritage Colchester, 195 Bagot Street, Colchester, ON

A vibrant community market celebrating local makers, artists, food vendors, and Colchester’s rich heritage. Explore unique handcrafted goods, enjoy delicious treats, take part in historical tours, and connect with local organizations while supporting the restoration of Colchester Schoolhouse #2. 🌿🏡

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🍽️ September 4, 5 & 6 – Windsor Food Festival 4.0
Sep 4–6 • 4:00 PM – 12:00 AM | Riverside Festival Plaza, Windsor

Experience one of Windsor's biggest celebrations of food, culture, and entertainment! Enjoy a weekend filled with delicious food vendors, food trucks, live performances, cultural experiences, and family-friendly fun along the waterfront. 🌮🎶🎉

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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.

🎷Chimczuk Museum: 50 Years of Jazz Concert Promotion in Windsor
August 13–20 — Chimczuk Museum, Windsor
Curated by Hugh & Kathy Leal, this new temporary display explores the history of jazz concert promotion in the Windsor area. Since the 1970s, Hugh & Kathy have been bringing jazz pioneers to Windsor and organizing concerts and recording sessions.

🎶Live at the Lighthouse
August 13 and 20 · 7:00pm — Mettawas Park Kingsville
Join us every Thursday throughout July and August for a free evening of live music at the gazebo next to the Lighthouse, located at 85 Park Street in Kingsville. This all-ages concert series is open to everyone.

🎸Leamington’s Music Onthe42 Summer Concert Series – Mystic Highway: CCR/Fogerty Tribute
Saturday, August 15 — SUNSET® Amphitheatre
The Municipality of Leamington is excited to announce the full lineup for the 2026 Music Onthe42 Summer Concert Series, returning to the SUNSET® Amphitheatre at Seacliff Park with free live music all summer long!

🎸 August 15 – 89NEXT Rocks with Windsor Premier Cruises
7:00 PM – 11:00 PM | Windsor Premier Cruises
Set sail along the Windsor–Detroit shoreline for an unforgettable evening of live alternative and rock music aboard the Macassa Bay. 89NEXT will perform favourite hits from the ’90s, 2000s, and beyond while the cruise travels beneath the Ambassador and Gordie Howe International Bridges

🎶 August 16 – Summer Sundays with Cherry Rock Lounge & 89X
7:30 PM – 10:00 PM | Cherry Rock Lounge, Windsor
Keep the weekend going with Summer Sundays at Cherry Rock Lounge in partnership with 89X! Enjoy an evening filled with cold drinks, great vibes, and live music as the Sunday night celebration keeps the summer energy going

🎶 August 16 – Pavlo in Concert
7:00 PM | Kingscoast Estate Winery, Kingsville
Spend an unforgettable evening under the stars as Pavlo returns to Kingsville with his world-class band for an intimate concert surrounded by beautiful vineyards.

🎶 August 16 – 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, delicious food, great wine, and good company

🎤 August 16 – Walk Off The Earth & Andy Grammer
7:30 PM | The Colosseum at Caesars Windsor
Get ready for an exciting night of live music as Walk Off The Earth and Andy Grammer bring their Big Stupid Heart Tour to The Colosseum at Caesars Windsor.

🎸 August 20 – John Fogerty: The Legacy Tour
8:00 PM | The Colosseum at Caesars Windsor
Rock legend John Fogerty brings his Legacy Tour to The Colosseum at Caesars Windsor for an unforgettable night of music.

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

😂Alexa Stanton LIVE Comedy At Tipsy Toucan (Aug 15th)
Saturday, August 15 · 8:00pm — The Tipsy Toucan, Windsor
Alexa may have the same name as a robot, but she doesn’t let that keep her down. She is a traveling Michigander that enjoys telling tales of her outlandish life to rooms full of people.

😂Rum Runners Tour – SOLD OUT
Sunday, August 16 — Rockstar Music Hall
Step back into the Roaring Twenties with The Rum Runners Tour — the award-winning theatrical adventure everyone’s raving about! Hop aboard for a 4-hour thrill ride filled with gangsters, rumrunners, comedy, music, and a lively speakeasy lunch show.

😂Phogheads comedy showcase
Tuesday, August 18 — Phog Lounge, Windsor
Looking for a reason to get off the couch this Tuesday? Every week, Phogheads transforms into one of Windsor’s most fun and intimate comedy rooms.

🎉Windsor International Black Film Festival
August 13–16 | Armouries Theater, Windsor
The Windsor International Black Film Festival (WIBFF) Presented by Black Scholars Institute (BSI) returns for its 2026 edition, presenting four days of powerful storytelling, industry engagement, and cultural celebration.

Chrysler Theatre AUGUST Youth Summer Camp
August 13–20 — The Chrysler Theatre, Windsor
9:00 AM- 4:00 PM Monday-Friday Your performers can sing, dance and act on The Chrysler Theatre stage for our annual Summer Camps! Led by experienced instructors, your child will have a blast playing games, learning techniques, and performing.

Capitol Arts Camp: Week 1- Explore the Arts
August 13–14 — Capitol Theatre Windsor, Windsor
Kids will explore a variety of art forms including theatre, music, singing, dance and film, all leading to an end of the week Camp Showcase for families and friends!

🎉WIDA Fest
August 20 | Lanspeary Park
WIDAFEST 2026 is Windsor’s celebration of African and Caribbean heritage. Running from August 20 to 23 at Lanspeary Park, this all-ages, free-entry festival features an inclusive gathering of music, art, food, and dance.

🎉Windsor International Diaspora African Festival
August 20 | Lanspeary Park
Celebrate the rich cultural heritage, creativity, and history of Africa and the African Diaspora at the Windsor International Diaspora African Festival.

🚗Ouellette Car Cruise
Friday, August 14 — Downtown Windsor
The Ouellette Car Cruise builds on the nostalgia of Windsor’s storied automotive history and seeks to engage car enthusiasts, hobbyists and the community at large in celebration of our deep automotive roots. Cruisers begin gathering at Riverfront Festival Plaza in the heart of downtown Windsor.

🃏RAD Sports Card & TCG Show
Saturday, August 15 · 10:00am — St Clair College Sportsplex, Windsor
The Rad Sports Card And TCG Show is back August 15th at the St. Clair College SportsPlex from 10am-4pm! 100+ vendor tables of sports cards and Pokémon, special guests, and raffle prizes!

“A Snowtastic Summer Celebration” Sing-Along Show
Saturday, August 15 · 3:00pm — The KordaZone Theater, Windsor
Join us for a fun sing-along show perfect for families, sponsored by Thiessen Apple Orchards! Dress up and sing along to some of your favourite songs performed by everyone’s beloved characters, The Frosty Trio.

🎬 August 17 – Summer Film Camps for Kids & Youth
See event details | Windsor Centre for Film, Digital Media and the Creative Arts, Windsor
Give young creators the chance to explore the world of film and digital media at Summer Film Camps for Kids & Youth. This popular educational program, offered by the Media Arts Community Centre & Museum and the Windsor Centre for Film, Digital Media and the Creative Arts, welcomes children and teens ages 8 to 17. Since beginning as a small research project in 2012, the program has grown into a high-demand summer experience designed to introduce youth to creative arts and media.

Enjoy markets, shows, fashion at Windsor.

🎨AWE Summer Nights
Thursday, August 13 — Art Windsor Essex
There’s something new happening this summer. July Summer Nights! July 2nd: Sip & Paint Join us for a relaxing night of painting, led by an artist educator & enjoy wine provided by Cooper’s Hawk Vineyard! Get tickets here!

🚴The Great Waterfront Trail Adventure
Thursday, August 13 — Various Locations
Join us from Monday , August 10th to Friday, August 14th, for the 2026 Great Waterfront Trail Adventure cycle tour and awareness ride. 5 Days |425km.

🎉 August 14 – Mill St. Market: Harvest, Place and Taste
5:00 PM – 10:00 PM | Mill Street West, Leamington
Celebrate Leamington’s agricultural roots at Mill St. Market – Harvest, Place and Taste, a free, family-friendly street festival highlighting the best of the region. Enjoy locally grown food, handcrafted goods, diverse culinary offerings, local craft beer, wine, creative cocktails, and a lively lineup of live entertainment.

🎨AWE Summer Nights
Thursday, August 20 — Art Windsor Essex
There’s something new happening this summer. July Summer Nights! July 2nd: Sip & Paint Join us for a relaxing night of painting, led by an artist educator & enjoy wine provided by Cooper’s Hawk Vineyard!

🍰 August 16 – Baking Series Workshop: Italian Desserts
1:00 PM – 5:00 PM | St. Clair College, Windsor
Discover the joy of baking at this interactive Italian Desserts Workshop, where participants will work alongside a professional pastry chef to create a delicious dessert to take home

🥃 August 20 – J.P. Wiser’s Distillery Experience: Tours & Tastings
See event details | J.P. Wiser’s Experience, Windsor
Celebrate Prohibition Week with a special, limited series of J.P. Wiser’s Distillery Tours. Discover the fascinating story of Canadian whisky, from its rich history and Prohibition-era connections to the craftsmanship and traditional processes behind its production.

🍣Kona Sushi Masterclass
Thursday, August 20 — Kona Lakeshore
Have you always wished to learn how to make your own sushi? Know is your chance with these professional classes that teach you everything you need to know!

🌆Amherstburg Open Air Weekends
August 14–16 — Downtown Amherstburg
Soak up the good vibes at Amherstburg Open Air Weekends, happening every Friday at 3pm to Sunday at 8pm in downtown! Snack on sweet treats and sip on delicious drinks – visit your favourite local dining spots. Browse the vendor market and local shops filled with unique finds.

🥕Downtown Windsor Farmers’ Market
Saturday, August 15 — Downtown Windsor Pelissier & Maiden Lane Windsor
At the Downtown Windsor Farmers’ Market you’ll find farm fresh fruit, vegetables, produce and unique artisan food products from the best our area has to offer.

🛍️ Tecumseh Farmers Market 2026
Sunday, August 16 · 9:00am — Lacasse Park, Tecumseh
TECUMSEH FARMERS MARKET Homemade. Homegrown. Handmade. Handsewn. Discover fresh, locally grown produce, handmade goods, and unique treasures from our talented local vendors. Join us each month and experience the best of what our region has to offer while supporting small businesses in the vibrant community of Tecumseh!

Chimczuk Museum: Treasures from the Vault
August 13–20 — Chimczuk Museum, Windsor
This temporary exhibition features fascinating artifacts from Museum Windsor’s collection. From recent acquisitions to unique items that have never been publicly displayed, this exhibit includes and eclectic mix of artifacts touching on various aspects of the region’s history.

🧺 Amherstburg Open Air Weekends – WEBC Cycle the Burg
August 14–16 — Downtown Amherstburg
Find everything you need in Amherstburg Open Air streets from craft beer, gourmet popcorn, cotton candy, frozen yogurt, gelato, baked goods to ice cream, satisfy your long awaited craving for delicious drinks and desserts from your favorite Amherstburg eateries.

Essex County Steam & Gas Engine Show
August 14–15 — Co-An Park
Step back in time and celebrate the golden age of farming and machinery at the Essex County Steam and Gas Engine Show!

Enjoy games, trivia and dinner nights in Windsor.

🌅August 13th Dinner & Cruise
Dinner 6:00pm, Cruise 8:00pm — St. Clair College Centre for the Arts, Windsor
Enjoy an unforgettable evening combining fine dining, stunning skyline views, and a relaxing river cruise. Begin your night with a delicious three-course plated dinner on the rooftop Viewpoint Terrace at the St. Clair College Centre for the Arts.

🌮 August 14 – Terrace Dinner: Mexico
7:00 PM | St. Clair College Centre for the Arts, Windsor
Enjoy a memorable evening of delicious food and stunning views at Terrace Dinners. This special four-course dinner features a Mexico-inspired menu served on the rooftop terrace, where guests can dine while taking in beautiful views of the Detroit skyline and waterfront.

🌌Dark Sky Nights – Point Pelee National Park
Thursday, August 13 — Point Pelee National Park
Explore the park after dark and experience the dark skies of Point Pelee National Park. You will have the opportunity to stay late and experience the park at night. Visitors can pick up a seasonal star chart at the front gate upon arrival.

🎬 August 14 – Moonlight Movie Night
8:30 PM | St. Mary’s Park, Maidstone
Enjoy a relaxing evening under the stars with a free outdoor movie at St. Mary’s Park! Bring along a blanket or lawn chair, some bug spray, and your favourite people, then settle in for a fun night of cinema on the big screen

🤠 August 15 – Kingsville Block Party: Country Night
5:00 PM – 10:00 PM | Kingsville Centre
Get together with friends and family for Kingsville Block Party – Country Night! Held on the third Saturday of the summer months, this lively community celebration brings together great local food and drinks, vendors, live entertainment, and plenty of fun

🎵 August 16 – Music Bingo Trivia at Walkerville Brewery
5:00 PM – 7:00 PM | Walkerville Brewery, Windsor
Put your music knowledge to the test at Music Bingo Trivia, hosted by Mack Flash Entertainment! Held one Sunday each month, this fun-filled evening combines a little bingo, a little trivia, and a whole lot of music.

🎲 August 17 – Card Board Game Night
5:00 PM | The Shadowbox Theatre, Windsor
Sally forth for an evening of board games and card games at The Shadowbox Theatre! Held on the third Monday of every month, Card Board Game Night is a fun and welcoming opportunity to play your favourite games, meet new people, and connect with fellow game enthusiasts

⛸️ August 15 – PLAY FOR FREE! WFCU Centre FREE Skating
6:00 PM – 8:00 PM | WFCU Centre
Lace up and enjoy a fun evening of free skating at the WFCU Centre! Part of Windsor’s Staycation Activation, this program offers free access to skating, swimming, curling, and golf at facilities across the city.

That's your week across Windsor-Essex. Whether you're catching John Fogerty at Caesars, dancing at WIDA Fest, or just grabbing fresh produce at a Saturday market, there's no shortage of ways to make the most of these long summer days. Get out there, support local, and we'll be back next week with another roundup of the region's best.

— Windsor Pulse