# Festivals in Winchester, ON | Cultural Events & Fairs - **Subtitle**: Explore upcoming festivals in Winchester, Ontario. Discover cultural celebrations, street fairs and seasonal events happening across the city. Join the festivities. - **Category**: Festivals - **Type**: category ## Audience - **Followers**: 2.5M+ - **Recent Followers**: - **Avatar 1**: https://cdn-az.allevents.in/events4/banners/c7a3bd77620a92a1fee77ed0b46cc305d65fcaf166695040aabebd480d9323a4-rimg-w200-h200-dc7e887a-gmir?v=1749580804 - **Avatar 2**: https://cdn-az.allevents.in/events2/banners/87514fe09e2e42afe6f2e6b5b9e483315429bdfa0a64d2af3268e7f6798e263a-rimg-w200-h200-dc182a60-gmir?v=1760132405 - **Avatar 3**: https://cdn-az.allevents.in/events4/banners/4372fbe0-97b1-11f0-925d-a7ce5707d3d8-rimg-w200-h200-dc445c46-gmir ## About The best things to do in the world include attending top-notch festivals in [CITY]. Be it a rocking music festival or scrumptious food festival in [CITY], you will have a gala time of your life with a few of your close friends or your family. With the best of fun, entertainment, and food, the experience in festivals lets the enthusiasts immerse in the local culture and vibe. Ranging from the biggest outdoor beach parties to crazy music festivals, the festivals fall under various categories to suit everybody’s tastes. If you are looking for the best events and festivals in [CITY] listed on one platform - we have you covered. Immerse yourself in the mega dance festivals, electrifying music festivals, theatre & film festivals, quirky local festivals and more with us! ## Festivals Events in Winchester - **Event Name**: The 14th Annual Art on the Waterfront - **Description**: The 14th Annual Art on the Waterfront returns to downtown Chesterville, Ontario on Saturday, June 6, 2026, from 10:00 AM to 4:00 PM. Admission is free.Now in its 14th year, Art on the Waterfront transforms the streets along the Sout - **Date**: Sat Jun 06 2026 at 10:00 am – Sat Jun 06 2026 at 11:00 am (-04:00) - **Event URL**: https://allevents.in/winchester/the-14th-annual-art-on-the-waterfront-tickets/80006935748679 - **Venue**: Main Street - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OWMxNjc3MjZhZjk1LmpwZw.avif - **Price**: Free - **Categories**: art, music, entertainment, kids, open-mic, concerts, festivals - **Event Name**: 14th Annual Art on the Waterfront - **Description**: Join us for the 14th Annual Art on the Waterfront — a free, one-day outdoor festival in downtown Chesterville, Ontario on Saturday, June 6, 2026. Explore a market of 60+ local artists and artisans, catch the Kids Talent Show at 11:00 AM, and drop into t - **Date**: Sat Jun 06 2026 at 10:00 am (-04:00) - **Event URL**: https://allevents.in/winchester/14th-annual-art-on-the-waterfront/200029832442652 - **Venue**: Main St., Chesterville, ON, Canada, Ontario K0C 1H0 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy82NjMzODhlNzkxMzMwYjE5MmMzZDAyNmU3NjFhOTQ2MzMzY2FjMmY1MGRkZDRmNzBmMDFjZDQ5N2E1YjYwZjZjLXJpbWctdzEyMDAtaDYzMC1kYzM0YmRlOS1nbWlyP3Y9MTc3NjE1ODA0NQ.avif - **Categories**: art, kids, festivals, open-mic, music, entertainment - **Event Name**: South Mountain Fair Demo Derby - **Description**: Kids Powerwheels - Free Midsize - $50 Trucks - $100 Max 10 Semi Stock Fullsize - $100 Max 10 Mini 3 Man Team - $200 FULL Registration opens April 1 for trucks and V8. - **Interested Audience**: - Count: 43 - **Date**: Thu Aug 13 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/winchester/south-mountain-fair-demo-derby/200029873661911 - **Venue**: South Mountain Fair - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy80ZDkxNzlkMDhiMTMzMGJiMWUwNDQ0OTU2NTdlODc3OWVkM2JjYjNlZjA4YzM5YTg2ZTY1MDdkYzRjY2JmZWI2LXJpbWctdzEwMjQtaDEwMjQtZGNmZWZlZmUtZ21pcj92PTE3NzU0Njk0MzQ.avif - **Categories**: kids - **Event Name**: The Outliers RC 3rd Annual Rodeo - **Description**: A fun day for the whole family - on and off the motorcycle. There will be games, prizes, a food vendor. $25 for the day. - **Interested Audience**: - Count: 119 - **Date**: Sun Jun 07 2026 at 10:00 am (-04:00) - **Event URL**: https://allevents.in/winchester/the-outliers-rc-3rd-annual-rodeo/200029323330600 - **Venue**: 2260 County Road 7 Chesterville - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9hMzVhMDg2YTg5ZGFhMDVmMjZjZjk3NTA3YmJlYmUxZTkzNDEyZTI3YWM5MDE4MzZjNmE2YWMzN2MwYTZjODcyLXJpbWctdzEyMDAtaDEyMDAtZGNlY2VkZjAtZ21pcj92PTE3NzU1NjU2NDc.avif - **Categories**: rodeo ## Trending Events in Winchester - **Event Name**: The 14th Annual Art on the Waterfront - **Description**: The 14th Annual Art on the Waterfront returns to downtown Chesterville, Ontario on Saturday, June 6, 2026, from 10:00 AM to 4:00 PM. Admission is free.Now in its 14th year, Art on the Waterfront transforms the streets along the Sout - **Venue**: Main Street - **Banner**: https://cdn2.allevents.in/thumbs/thumb69c167726af95.jpg - **Event Name**: Mother's Day Family Paint Day (6+ yrs)_LOVE BLOOMS - **Description**: Let's celebrate Mom this Mother's Day with art-from-the-heart!About this EventMother's Day Family Paint Day (Ages 6+) in Winchester, Ontario!🌷🌸🎨🌷🌸🎨🌷🌸🎨Join Ms. Rose for a fun - **Venue**: Sam Ault Arena - **Banner**: https://cdn-az.allevents.in/events6/banners/1a8eb512c59b45fa8b56c2ec60b7db59f33e26a9244e74784ed36edfcc59ce0a-rimg-w1200-h400-dcfed760-gmir.jpg?v=1773143368 - **Event Name**: North Dundas Local Business Expo 2026 - **Description**: Saturday, April 25th from 9:00am-3:00pm Joel Steele Community Centre, 577 Main St, Winchester Bring the whole family for a full day of fun! ***Get excited for the “Cardboard and Lego Extravaganza” kids play area*** - Explore and visit 100 exhibitors: S - **Venue**: 577 Main Street, Winchester, Ontario - Joel Steele Community Centre - **Banner**: https://cdn-az.allevents.in/events6/banners/99c5c19ac817072c25207fd497156e30461efe1f3ece1fa89b6c829fd47b5e41-rimg-w1200-h900-dc16191b-gmir?v=1775899739 - **Event Name**: 14th Annual Art on the Waterfront - **Description**: Join us for the 14th Annual Art on the Waterfront — a free, one-day outdoor festival in downtown Chesterville, Ontario on Saturday, June 6, 2026. Explore a market of 60+ local artists and artisans, catch the Kids Talent Show at 11:00 AM, and drop into t - **Venue**: Main St., Chesterville, ON, Canada, Ontario K0C 1H0 - **Banner**: https://cdn-az.allevents.in/events9/banners/663388e791330b192c3d026e761a946333cac2f50ddd4f70f01cd497a5b60f6c-rimg-w1200-h630-dc34bde9-gmir?v=1776158045 - **Event Name**: Garden Party Mother’s Day Market - **Description**: We are excited to bring over 30 artisan vendors, live music, games, children’s entertainment and bouncy castles together for a fun and interactive Market for families to enjoy. Stay tuned for more details and vendor information - **Venue**: The Winchester Arena - **Banner**: https://cdn-az.allevents.in/events9/banners/c82a78633a484eb38daa96db37434882dbe61647a78f24ecd567e4d84be4ab7d-rimg-w1024-h1536-dcf0f5f1-gmir?v=1776040003 - **Event Name**: Russell Legion Annual Golf Tournament - **Description**: ⛳️ **WOW — we can’t believe it already!** ⛳️ People are already reaching out to **lock in their teams** so they don’t miss out on our **2026 Russell Legion Annual Golf Tournament** — and we love the excitement! This tournament is always a **huge hit**, - **Venue**: Cloverdale Links Golf Course - **Banner**: https://cdn-az.allevents.in/events8/banners/3fb400f25929228f5aca2b850fbb49ae21d55e7dfa250a138a4089281f0a6dd0-rimg-w1200-h1553-dc7e9046-gmir?v=1775362136 - **Event Name**: South Mountain Community Yard Sale 2026 - **Description**: South Mountain Community Yard Sale ! Saturday May 9th, 2026 Come out and enjoy a stroll around South Mountain and find some great deals! Vendors, food ect! 🌸Plus its Mother's Day weekend! 🌷 Come out and bring mom and find some treasures and take - **Venue**: South Mountain, Ontario - **Banner**: https://cdn-az.allevents.in/events9/banners/af058649adf85ce0574c03f8b9249cc1a1dc211c7202338bb48cbdd19e268fbe-rimg-w904-h1280-dcffffff-gmir?v=1774689752 - **Event Name**: Amanda and Kurtis’ Stag & Doe - **Description**: Amanda and Kurtis are tying the knot 💍🥂 Come celebrate with us on May 9th upstairs at the Winchester Arena. It will be a night filled with dancing, drinks, games, food and unforgettable memories! 💃🏼🕺🏻 Make sure to bring cash for the raffle as there wil - **Venue**: The Winchester Arena - **Banner**: https://cdn-az.allevents.in/events7/banners/20f8867c7187f0cd7fefa8e7373fe9d91ddf8778002d869eccb301400495ff01-rimg-w1042-h1560-dc2e3117-gmir?v=1773635421 - **Event Name**: SDG Geek-Con 2026 - **Description**: We are **so excited** to bring the event back to the **SDG area**!! 🌟 --- **🗓️ Admission:** 💵 $5 at the door 👶 Kids 12 and under are **FREE** with a paying adult! --- This event will showcase an **array of 60+ vendors** offering all things **nerdy, ge - **Venue**: Chesterville and District Arena - **Banner**: https://cdn-az.allevents.in/events6/banners/ac62c6add62c34551e32a3de241e325193c6e51c4451b994fef10650d876f475-rimg-w1200-h800-dcf8fe01-gmir?v=1776117120 ## Browse Festivals Events by Date - [Festivals Events Today in Winchester](https://allevents.in/winchester/festivals--today) - [Festivals Events This Weekend in Winchester](https://allevents.in/winchester/festivals--this-weekend) - [Festivals Events in April in Winchester](https://allevents.in/winchester/festivals--april) - [Festivals Events in May in Winchester](https://allevents.in/winchester/festivals--may) ## FAQs - **Q**: What are the top Festivals events in Winchester? - **A:** The 14th Annual Art on the Waterfront (Sat Jun 06 2026 at 10:00 am at Main Street), 14th Annual Art on the Waterfront (Sat Jun 06 2026 at 10:00 am at Main St., Chesterville, ON, Canada, Ontario K0C 1H0), South Mountain Fair Demo Derby (Thu Aug 13 2026 at 07:00 pm at South Mountain Fair), The Outliers RC 3rd Annual Rodeo (Sun Jun 07 2026 at 10:00 am at 2260 County Road 7 Chesterville). - **Q**: What are the top free Festivals events in Winchester? - **A:** The 14th Annual Art on the Waterfront (Sat Jun 06 2026 at 10:00 am at Main Street). - **Q**: How can I find Festivals events in Winchester? - **A:** You can discover upcoming Festivals events in Winchester on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Festivals events in Winchester? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Festivals events in Winchester? - **A:** Some popular venues hosting Festivals events in Winchester include Main Street, Main St., Chesterville, ON, Canada, Ontario K0C 1H0, South Mountain Fair. - **Q**: Who are the top organizers for Festivals events in Winchester? - **A:** Popular organizers hosting Festivals events in Winchester include Art on the Waterfront, Art on The Waterfront, Ontario Demolition. - **Q**: Are there any online Festivals events available? - **A:** Yes, many Festivals events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Festivals events in Winchester? - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Winchester. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/6e/5415e403f74b77938c0695ac11464e/Festival.jpg ## Festivals from nearby cities - [Festivals in Embrun](https://allevents.in/embrun/festivals) - [Festivals in Kemptville](https://allevents.in/kemptville/festivals) - [Festivals in Ingleside](https://allevents.in/ingleside-on/festivals) - [Festivals in Casselman](https://allevents.in/casselman/festivals) - [Festivals in Gloucester](https://allevents.in/gloucester-ca/festivals) - [Festivals in Nepean](https://allevents.in/nepean/festivals) - [Festivals in Prescott](https://allevents.in/prescott-on/festivals) - [Festivals in Cornwall](https://allevents.in/cornwall-on/festivals)