There’s always something happening in the 1000 Islands! From waterfront concerts and boat shows to food festivals and fishing derbies, the region is packed with events year-round. Enjoy live music by the river, savor local flavors at culinary celebrations, or experience the thrill of seasonal festivals. No matter when you visit, there’s an event to make your adventure unforgettable.
Upcoming Events to Discover in Brockville, ON
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Nov 28 @ 7:00 PM - 9:00 PM EST | Arts Hub Brockville
The Maywoods @ Festival of Small Halls Ontario
The Maywoods perform a John Prine experience featuring rich harmonies, multi-instrumental arrangements, storytelling, and sing-alongs.
Explore eventNov 28 @ 7:30 PM EST | Kingston Grand Theatre, Rosen Auditorium
Classic Albums Live – The Stranger (Billy Joel)
A live performance of Billy Joel’s album The Stranger by Classic Albums Live.
Explore eventNov 28 @ 7:30 PM EST | The Spire
Classic Troubadours Live
A live tribute performance celebrating the music of classic troubadours, presented at The Spire in Kingston.
Explore eventDec 2 @ 12:00 AM EST | Waterfront Gifts & Apparel / Kingston Trolley Tours departure point
Christmas Light Tour
A 75-minute festive trolley ride through Kingston’s decorated neighbourhoods and downtown streets, with holiday commentary from an elf and driver and views of seasonal light dis...
Explore eventDec 3 @ 7:00 PM - 11:00 PM EST | Kingston Grand Theatre
Bored Teachers Is it Friday Yet?! Comedy Tour
They’ve graded the papers, survived the staff meetings, and lost their last ounce of patience… and now they’re taking it out on stage! Bored Teachers is BACK with brand-new joke...
Explore eventDec 4 @ 12:00 AM EST | Fulford Place
Candlelight Christmas Tours
Evening candlelight tours of Fulford Place following the Christmas open house, with seasonal decorations and a holiday experience in the historic mansion. The published 2026 dat...
Explore eventDec 4 @ 5:30 PM EST | Dulles State Office Building
A North Country Festival of Trees Gala
An evening holiday event with food, music, and a live tree auction presented by the Watertown Family YMCA and Samaritan Medical Center Foundation. The 2026 festival runs Novembe...
Explore eventDec 4 @ 6:30 PM EST | Clayton Opera House
The Polar Express Interactive Movie Experience
An interactive screening of The Polar Express with the Butler Did It Players. Guests can bring a sleeping bag or lawn chair, meet the conductor, receive a punched Believe ticket...
Explore eventDec 4 @ 6:30 PM EST | Clayton Opera House, 405 Riverside Dr, Clayton, NY 13624-1024, United States
"The Polar Express" Interactive Movie Experience
The Polar ExpressFriday, December 4, 6:30pm. Sponsored by Steve and Betsy Dubois An Interactive Movie Experience with The Butler Did It Players. Stop by the Clayton Opera House...
Explore eventDec 4 @ 7:30 PM - 10:00 PM EST | 305 Rideau Street, Kingston, ON K7K 3A9
Tommy Youngsteen- Fleetwood Mac "Rumours" LIVE
Tommy Youngsteen performs Fleetwood Mac's classic 1977 album "Rumours" Along with all their Greatest Hits!
Explore eventDec 5 @ 12:00 AM EST | Downtown Clayton
64th Annual Clayton Christmas Parade & Fireworks
Clayton's annual downtown holiday parade followed by fireworks over the riverfront. The 64th annual event is scheduled for Saturday, December 5, 2026, as part of Clayton's Chris...
Explore eventDec 5 @ 10:00 AM - 1:00 PM EST | F.X. Caprara Harley-Davidson of Adams Center
Pics with Santa and Krampus!
Bring your festive spirit and meet Santa. Harley dogs, bike lovers, and people of all ages are welcome.
Explore eventDec 5 @ 10:00 AM - 3:00 PM EST | Thousand Islands Arts Center
The Elves Fair
A family-friendly holiday craft fair featuring crafts, fine art and fine craft exhibitors, kids’ crafts, gift wrapping, hot cocoa, and seasonal shopping.
Explore eventDec 5 @ 10:00 AM - 4:00 PM EST | Thousand Islands Winery
2026 Kris Kringle Market
Get ready to jingle and mingle at the 2026 Kris Kringle Market, where festive cheer and unique gifts await!
Explore eventDec 5 @ 11:00 AM - 3:00 PM EST | Thousand Islands Arts Center
The Elves’ Fair
A free, family-friendly juried holiday art and craft market featuring handmade gifts, artwork, seasonal decor, artisanal treats, and local vendors.
Explore eventDec 5 @ 12:00 PM - 4:00 PM EST | Frink Park and Clayton Opera House
1000 Islands River Santa Festival
Holiday family festival for children age 12 and under. Santa arrives at Frink Park at 1:00 p.m.; gifts and activities take place at the Clayton Opera House from noon to 4:00 p.m...
Explore eventDec 5 @ 4:00 PM EST | Dulles State Office Building
Performance by Dance World
A festive dance performance by Dance World presented as part of A North Country Festival of Trees, featuring high-energy routines and holiday entertainment.
Explore eventMultiple Dates | Prescott Pop-Ups
RiverWalk Wonderland
Interactive holiday event at the Prescott Pop-Ups featuring an annual tree lighting, live Christmas music, games and activities, a vendor market, refreshments, photos with Santa...
Explore eventDec 5 @ 6:00 PM - 6:20 PM EST | Blockhouse Island parking lot
AQ Holiday Train
A free 20-minute holiday train ride departing from the Blockhouse Island parking lot and making two festive laps around Brockville’s River of Lights. Complimentary hot chocolate...
Explore eventDec 5 @ 6:00 PM EST | Downtown Clayton
64th Annual Christmas Parade & Fireworks
Clayton’s annual Christmas parade and fireworks display. The 2026 theme is “Stars, Stripes & Christmas Lights.”
Explore eventDec 6 @ 10:00 AM - 1:00 PM EST | The Lincoln Loft
Holiday Maker's Market
A holiday market featuring local makers, crafters, and artists at The Lincoln Loft in downtown Watertown. Visitors can shop for handmade and locally produced gifts while support...
Explore eventDec 6 @ 2:30 PM - 4:30 PM EST | The Lincoln Loft
Holiday Wreath Class w. Jennifer Rose Designs
A hands-on holiday wreath-making class led by Jennifer Rose Designs. Participants create a custom 12-inch wreath using fresh greenery, seasonal accents, dried fruit, ribbons, pi...
Explore eventDec 12 @ 12:00 AM EST | HHPAA Field
Town Christmas Celebration
Town Christmas Celebration listed by the Henderson Business & Community Council in the 2026 Henderson/Henderson Harbor community calendar. The event is listed at HHPAA Field.
Explore eventDec 12 @ 9:00 AM - 10:30 AM EST | Madymae on Broadway
DENFIT Jingle Bell 5k
An ugly-sweater holiday family fun run through Cape Vincent village streets. The untimed 5K includes jingle bells, holiday refreshments, an ugly-sweater gift-certificate raffle,...
Explore eventDec 12 @ 2:00 PM - 4:30 PM EST | Brockville Arts Centre
Christmas in the Valley with Wayne Rostad, Bobby Lalonde & Friends
A family-friendly Christmas concert featuring Canadian entertainer Wayne Rostad, Canadian Fiddle Champion Bobby Lalonde, Stag Creek, festive classics, holiday stories, and a San...
Explore eventDec 12 @ 3:00 PM EST | Trinity Concert Series
Hyde-Hall/Ramey Duo
A holiday four-hands piano concert blending virtuoso technique, seasonal warmth, classic carols, festive favorites, and joyful piano arrangements performed by Chris Hyde-Hall an...
Explore eventDec 13 @ 2:00 PM - 11:00 PM EST | 500 Newell Street, Watertown, NY 13601
1812 presents Small Town Titans, Scotty Austin former singer of Saving Abel
Live music featuring Small Town Titans, Scotty Austin, Bad Marriage, Shallow Side, Who On Earth, and more.
Explore eventDec 13 @ 3:00 PM EST | First Presbyterian Church Watertown
'Tis the Season — Watertown
A holiday concert by the Orchestra of Northern New York featuring favorite seasonal music.
Explore eventDec 16 @ 7:30 PM - 8:00 PM EST | 675 Development Drive, Kingston, ON K7M 4W6
Small Town, Big Laughs – Live Stand-Up Comedy in Kingston
Small Town, Big Laughs is coming to Kingston for one-night only! Watch amazing comedians right here in Kingston!
Explore eventDec 17 @ 7:00 PM - 11:00 PM EST | Royal Theatre Thousand Islands
The Royal Singers Christmas Concert
The Royal Singers Christmas Concert
Explore eventDec 17 @ 7:30 PM - 9:45 PM EST | Brockville Arts Centre
Natalie Macmaster & Donnell Leahy: A Celtic Family Christmas
Get ready for the brand-new Celtic Family Christmas...PARTY! You’ll have plenty of time to sip eggnog by the fire, but not on this night... So buckle up and join Natalie MacMast...
Explore eventDec 18 @ 8:00 PM - 11:00 PM EST | 193 Ontario Street, Kingston, ON K7L 2Y7
A Celtic Christmas
The Celtic Kitchen Party playing a mix of upbeat Christmas favs, Celtic infused originals, and traditional and contemporary Celtic music.
Explore eventDec 19 @ 2:00 PM - 4:00 PM EST | The Lincoln Loft
Holiday Charcuterie Class w. Lisa's Cucina
A hands-on holiday charcuterie class led by Lisa's Cucina. Guests learn to build a balanced charcuterie board, receive a guided demonstration, enjoy a complimentary glass of win...
Explore eventJan 28 @ 7:00 PM - 9:45 PM EST | Brockville Arts Centre
Cinderella by The United European Ballet Company
Cinderella is a full-length classical ballet set to the beautiful and expressive music of composer Sergei Prokofiev. This timeless fairy tale tells the story of a kind young wom...
Explore eventJan 29 @ 7:00 PM - 9:30 PM EST | Brockville Arts Centre
Hotel California: The Original Eagles Tribute
When The Eagles stopped to catch their breath a few decades ago, having sold over 100 million records, collected six Grammy’s, and enjoyed six #1 albums, Hotel California began...
Explore eventFeb 19 @ 7:00 PM - 9:00 PM EST | Joshua Bates Centre
Suzie Vinnick & Tony D.
An evening concert featuring acclaimed Ontario blues and roots performers Suzie Vinnick and Tony D. Suzie Vinnick is a multiple Maple Blues Award winner and Juno nominee; Tony D...
Explore eventFeb 21 @ 8:00 AM - 3:00 PM EST | Winona CCC
Winona’s Tired Iron Vintage Show & Ride
A vintage snowmobile show and ride at Winona CCC. Registration runs from 8:00–10:00 AM, judging from 10:00 AM–12:00 PM, lunch and awards from 12:00–1:00 PM, followed by the vint...
Explore eventFeb 27 @ 8:00 AM - 4:00 PM EST | Cape Vincent Recreation Park
DENFIT Winter Soldier
Winter road race with 10K, half-marathon, and full-marathon options. The course runs from Cape Vincent Recreation Park toward Tibbetts Point Lighthouse and back, with a heated s...
Explore eventMar 6 @ 11:00 AM - 5:00 PM EST | 33 Benson Street, Kingston, ON K7K 6X4
FANATICCON KINGSTON
FANATICCON KINGSTON is a fan convention celebrating Toys, Comics, Gaming, Art, Anime, TCG, Cosplay, Entertainment and more
Explore eventMar 13 @ 7:00 PM - 9:00 PM EST | Joshua Bates Centre
Outskirts: Celebrating the Music of Blue Rodeo
A live performance by Eastern Ontario six-piece Outskirts, celebrating the music of Blue Rodeo with country-rock songs, familiar hits, deeper album cuts, ballads and harmonies.
Explore eventApr 3 @ 8:00 PM - 10:00 PM EDT | 82 Sydenham Street, Kingston, ON K7L 3H4
André Bisson Band Live at The Spire! 2027
Join us for an evening of Soul, Blues, and Folk music! High energy songs combined with musical storytelling performed with a 7-piece band
Explore eventApr 17 @ 7:00 PM - 9:00 PM EDT | Joshua Bates Centre
Beatle Nation
A Beatles tribute concert featuring era-authentic costumes, harmonies, and songs spanning the band’s early Liverpool performances, the Shea Stadium era, the Apple Records years,...
Explore eventMay 15 @ 8:00 AM - May 16 @ 8:00 AM EDT | Winona Forest CCC Camp
Winona Forest's Chase the Day Trail Ultra
A timed trail ultra and outdoor festival offering 6-hour, 12-hour, 24-hour, and three-person team options on an approximately 2.65-mile loop. The event includes food, fireside s...
Explore eventMay 15 @ 7:30 PM - 9:00 PM EDT | 5 Wall Street, Brockville, ON K6V 4R8
Brockville: Saturday, May 15, 2027 – 7:30 PM: Beatles Tribute
Brockville: Saturday, May 15, 2027 at 7:30 PM – Candlelight Beatles Tribute
Explore eventJun 19 @ 7:30 PM - 9:00 PM EDT | 5 Wall Street, Brockville, ON K6V 4R8
Brockville - Saturday , June 19, 2027 at 7h30 PM : Tribute to Pink Floyd
Brockville - Saturday , June 19, 2027 at 7h30 PM : Tribute to Pink Floyd
Explore eventJul 3 @ 12:00 PM - 1:30 PM EDT | Outlook Avenue
Thousand Island Park 5K
The Thousand Island Park 5K, also called the General TJ Costello Memorial Footrace, is a family-oriented memorial 5K through Thousand Island Park. The course includes dirt roads...
Explore eventJul 3 @ 12:00 PM - 1:30 PM EDT | Outlook Avenue
Thousand Island Park 5K
The Thousand Island Park 5K, also called the General TJ Costello Memorial Footrace, is a family-oriented memorial footrace honoring General TJ “Demon” Costello. The scenic cours...
Explore eventJul 4 @ 7:00 AM - 11:00 AM EDT | Cape Vincent East End Waterfront Park
DENFIT 1776
Fourth-of-July run with 7.76-mile and 17.76-mile challenge options beginning at Cape Vincent East End Waterfront Park. Participants carry or display American flags while followi...
Explore eventJul 17 @ 12:00 AM EDT | Henderson Harbor Yacht Club
HHWSP Gala and Auction
Annual gala and auction benefiting Henderson Harbor Water Sports Programs, held at the Henderson Harbor Yacht Club.
Explore eventJul 24 @ 12:00 AM EDT | Upper James Street Docks
48th Annual Show
Annual antique and classic boat show presented by the Antique and Classic Boat Society. The event is scheduled at the Upper James Street Docks in Alexandria Bay; additional deta...
Explore eventAug 1 @ 8:00 AM - 12:00 PM EDT | Centeen Park
Thousand Islands Triathlon & Runs
A Brockville waterfront endurance event with race options ranging from 5K runs to Olympic-distance triathlon events. The course includes a run through Brockville’s historic rail...
Explore eventAug 21 @ 12:00 AM EDT | Winona Forest Recreation Area
Winona Forest Backyard Ultra
A last-runner-standing trail race in the Winona Forest Recreation Area. Participants complete a 4.167-mile loop beginning each hour and continue until only one runner remains. T...
Explore eventSep 18 @ 7:30 PM - 9:00 PM EDT | 82 Sydenham Street, Kingston, ON K7L 3H4
Kingston - Saturday , September 18, 2027 at 7h30 PM : Tribute to Pink Floyd
Kingston - Saturday , September 18, 2027 at 7h30 PM : Tribute to Pink Floyd
Explore eventOct 23 @ 7:30 PM - 9:00 PM EDT | 5 Wall Street, Brockville, ON K6V 4R8
Brockville : Saturday, October 23, 2027 at 7h30 : Elvis Fever
Brockville : Saturday, October 23, 2027 at 7h30 : Elvis Fever
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