📅 Updated Monthly
Okanagan Events Calendar
Your monthly guide to what’s happening across the valley — festivals, markets, concerts, wine events, sports, and community happenings from Penticton to Osoyoos and everywhere in between.
⭐ Don’t Miss These
Featured Events — May 2026
The biggest events happening this month across the Okanagan. These are the ones worth planning your calendar around.
May 28 – 31
18th Annual Half Corked Marathon
📍 Oliver Osoyoos Wine Country — Black Sage Road & Golden Mile
The South Okanagan’s most beloved wine-and-run event returns for its 18th year. A 20–24km costumed run through the vineyards with winery stations pouring along the route. Weekend includes Tailgate Party (Thu), Block Party at Nostalgia Wines (Fri), Race Day with Finish Line Party (Sat), and Dinner at the Farm (Sun). Creative costumes required — prizes for best individual, team, and skit.
May 1 – 3
Pig Out Festival — Let’s Feast
📍 Cellar Door & More, Oliver
One of the South Okanagan’s most indulgent weekends kicks off the month. Sixteen chefs, BBQ masters, butchers, and producers take the stage at vineyard stations with unlimited bites, local wines, and live music. Kickoff dinner at Sweetgrass Restaurant on Friday May 1st with guest chefs from Vancouver. Sunday adds guided Pig Out Trails wine tours across the region.
May 14 – 18
Osoyoos Spring Music Festival
📍 Various Venues, Osoyoos · Free & Ticketed
Osoyoos’s beloved spring celebration — multiple days of live music at venues across town spanning country, blues, and folk. One of the first major music events of the Okanagan summer season, drawing visitors from across the valley to Canada’s warmest town before the peak summer crowds arrive.
Every Saturday — All Month · 8:30 AM – 1:00 PM
Penticton Farmers’ Market
📍 100 Block Main St, Downtown Penticton
The South Okanagan’s most popular outdoor market runs every Saturday through May. Up to 90+ vendor stalls of farm-fresh produce, baked goods, handmade goods, local wine, beer, cider, and live buskers. Four new farm vendors joined the 2026 lineup — a Penticton Saturday morning institution since 1991.
📅 Full Calendar
May 2026 Events
Everything we’ve found happening across the Okanagan this month, organized by week. Dates and details are confirmed at time of publishing — always verify with the official organizer before attending.
Thu–Sun
May
🍖 Food Festival
Pig Out Festival — Let’s Feast
Three days of culinary indulgence in the vineyards. Kickoff chef’s dinner at Sweetgrass Restaurant on Friday, main festival Saturday with unlimited bites from 16+ chefs, BBQ masters, and producers paired with local wines and live music. Sunday adds guided Pig Out Trails wine tours across the region.
Oliver Festival Details →Sat
May
🌿 Nature
Osoyoos Desert Centre — 2026 Season Opening
Canada’s only pocket desert ecosystem opens its boardwalk trails and guided programs for the year. Spring is one of the best times to visit — wildflowers in bloom before summer heat peaks. Guided tours, interpretive exhibits, and a uniquely Okanagan outdoor experience.
Osoyoos Visit Details →Tue
May
🍽️ Food & Drink
International Oyster Day at the Sonora Room
The Sonora Room at Burrowing Owl celebrates International Oyster Day with a special tasting experience. A great excuse to visit one of the Okanagan’s top winery restaurants.
Penticton Event Info →Wed
May
🎵 Live Music
Nashville Rounds at Frog City Cafe
Songwriters performing in the round, sharing the stories behind their songs. One of Penticton’s most intimate live music formats.
Penticton Details →Wed
May
🎵 Live Music
Martin Harley at The Hub on Martin
British blues and roots artist Martin Harley brings his signature slide guitar sound to Penticton’s premier live music venue. Known for raw, intimate performances.
Penticton Details →Thu
May
🎵 Live Music
Robin Layne & The Rhythm Makers at Frog City Cafe
A full Thursday evening of Okanagan roots and rhythm. Mustang Musicians open at 6, followed by Robin Layne and The Rhythm Makers. Great energy in a great local room.
Penticton Details →Thu
May
🎵 Live Music
KINGA Quintet at The Hub on Martin
KINGA Quintet brings jazz-influenced ensemble music to Penticton’s main stage. A rich, layered sound for a spring Thursday evening — all welcome.
Penticton Details →Thu
May
🍷 Wine
Music Bingo at Vows & Vines Vineyard
Music bingo in a vineyard setting — a popular recurring Thursday event for groups and couples looking for something different in the valley.
Penticton Details →Thu
May
🎵 Live Music
Oh November at Cannery Brewing
Local indie act Oh November plays a free early-evening set at Cannery Brewing. Grab a pint on the patio at one of Penticton’s best neighbourhood breweries.
Penticton Details →Fri–Sun
May
🎨 Arts & Mother’s Day
Mother’s Day Weekend Events
Paint, Sip & Savour at River Stone Estate Winery (Fri May 8, 5:30 PM) and Build Your Own Bouquet at Sahara Garden Art (Fri May 8, 6 PM). Mother’s Day Sunday brings winery brunches and special tasting menus across the valley — book ahead, tables fill fast.
Penticton Event Info →Thu–Mon
May
🎵 Music Festival
Osoyoos Spring Music Festival
Osoyoos’s beloved annual spring celebration — multiple days of live music at venues across town spanning country, blues, and folk. One of the first big music events of the Okanagan summer season. A great excuse to make the drive south to Canada’s warmest town before the peak crowds arrive.
Osoyoos Destination Osoyoos →Sat
May
🛍️ Market
Downtown Community Market — 2026 Season Opener
Penticton’s Downtown Community Market opens its 2026 season on May 16. Handmade goods, clothing, food, jewellery, collectibles, and antiques — one of downtown’s biggest Saturday attractions. Runs alongside the Farmers’ Market every Saturday through early September.
Penticton Market Info →Sat–Mon
May
👨👩👧 Community
Victoria Day Long Weekend — Valley-Wide
The unofficial first weekend of Okanagan summer — beaches, trails, golf courses, and winery patios across the valley fill up fast. Osoyoos typically hits the warmest temperatures in BC this weekend. Great time to explore the Naramata Bench, the Okanagan River Trail, or settle onto a patio in Oliver wine country. Book accommodation ahead of time.
Valley-Wide Outdoor Guide →Thu
May
🍷 Wine Event
Half Corked — Tailgate Party ★ New for 2026
Brand-new for 2026 — kick off Half Corked weekend a day early with this casual vineyard Tailgate Party. Sample wines from across Oliver Osoyoos Wine Country while enjoying bites from local food trucks in a relaxed atmosphere. The perfect warm-up. Transportation not included.
Oliver Get Tickets →Fri
May
🍷 Wine Event
Half Corked — Block Party at Nostalgia Wines
Friday night’s Block Party at Nostalgia Wines — a multi-course feast through the vineyard blocks with live music and wine pairings. An elevated, festive evening ahead of race day. Transportation from Oliver and Osoyoos included with tickets.
Oliver Get Tickets →Sat
May
🍷 Festival & Run
18th Annual Half Corked Marathon — Race Day
The main event — 20 to 24km through the vineyards and river valley of wine country, winery stations pouring for costumed runners along the route, and a Finish Line Party to close it out. Costumes are essential — prizes for best individual, best team, and best skit. One of BC’s most genuinely fun outdoor events of the year.
Oliver Race Info →Sun
May
🍷 Wine Dinner
Half Corked — Dinner at the Farm
An intimate multi-course family-style feast outdoors on a scenic vineyard. A local chef prepares each course while a winemaker hosts each table, personally pairing wines and sharing their story. The perfect sophisticated finale to the Half Corked weekend. Dress appropriately for evening temperatures outdoors.
Oliver Dinner Details →🔁 Every Saturday · 8:30 AM – 1:00 PM
Penticton Farmers’ Market
📍 100 Block Main St, Penticton
🔁 Every Saturday from May 16 · 8:30 AM – 1:30 PM
Downtown Community Market
📍 Downtown Penticton
🔁 Every Friday
Fireside Fridays — Live Music & Perogies
📍 Backroads Brewing Co., Osoyoos
🔁 Weekly
Firehall Open Mic & Jam Night
📍 Firehall Brewery, Oliver
🔁 Weekly
Music Bingo — Backroads Brewing Co.
📍 Backroads Brewing Co., Osoyoos
🔁 Every Wednesday · 6:00 – 8:00 PM
Wine & Song Wednesdays — Maestro’s
📍 Maestro’s Mediterranean, Kelowna · 50% off wine bottles with live music
Know an event we should include?
If you’re organizing an event in the Okanagan Valley and would like it featured on next month’s calendar, drop us a line. We prioritize community events, festivals, markets, and family-friendly activities.
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Looking for events near a specific town? Our community pages cover life in every corner of the valley — including local events, recreation, food, schools, and real estate.
💡 Coming soon: Individual town event calendars for each South Okanagan community. Want to see events filtered by your town? Let us know — we’re building based on what readers actually want.
Back to top ↑❓ Common Questions
Events Calendar FAQ
Everything you need to know about using this events calendar, submitting events, and getting the most out of your Okanagan weekends.
What events are happening in the Okanagan this month?
May 2026 highlights include the Pig Out Festival in Oliver (May 1–3), the Osoyoos Desert Centre season opening (May 2), the Osoyoos Spring Music Festival (May 14–18), the Downtown Community Market season opener in Penticton (May 16), and the Half Corked Marathon weekend in Oliver Osoyoos Wine Country (May 28–31). The Penticton Farmers’ Market runs every Saturday. Check this page monthly for the latest listings.
Where can I find South Okanagan events?
This events calendar covers the full South Okanagan including Penticton, Oliver, Osoyoos, Summerland, Keremeos, Okanagan Falls, Cawston, and Princeton. We update it monthly with verified events from local tourism boards, venues, and community organizations. You can also check visitpenticton.com, destinationosoyoos.com, and oliverosoyoos.com for town-specific listings.
Are these events family-friendly?
Many events listed here are family-friendly, including the Penticton and Osoyoos farmers markets, the Osoyoos Desert Centre, the Downtown Community Market, and Victoria Day weekend community gatherings. The Half Corked Marathon and Pig Out Festival are primarily adult-oriented events with wine and alcohol as a central component. Always confirm details with the official organizer before attending with children.
How often is this events calendar updated?
We update this calendar at the beginning of each month with verified events for the upcoming 4–6 weeks. Featured events are confirmed with official organizers. If an event changes or cancels after we publish, we recommend checking the official event page linked in each listing for the most current information.
Can I submit an event to be featured?
Yes. If you are organizing an event in the Okanagan Valley and would like it featured on this calendar, contact us here with your event name, date, location, description, and a link to the official event page. We prioritize community events, festivals, markets, and family-friendly activities.
Do I need to confirm event details before attending?
Yes. Event details including dates, times, pricing, and locations can change on short notice. We recommend always confirming directly with the event organizer or official venue before making plans. Links to official event pages are included in each listing for easy verification.
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I’m Riccardo Manazza — a licensed REALTOR® with eXp Realty and a proud South Okanagan local. If you’re exploring communities, thinking about relocating, or ready to buy — I know this valley inside out and I’d love to help you find where you belong.
Event details are confirmed at time of publishing. Dates, times, pricing, and availability may change — always confirm directly with the event organizer or official venue before attending. This page is updated monthly by Living in the Okanagan. Last updated: May 2026.