"BRUSH & BLUFF" Paint Night
2025-12-11 17:00 - 20:00 UTC | Oliver Visitor Centre, 6431 Station Street British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Join Artists Karlie and Colleen at the Oliver Visitors Centre and paint your very own McIntyre Bluff scene, and enjoy a delicious appy spread made by Chef Colleen from OKGN2GO.

Paint, snack, and celebrate the season inside the Oliver Visitor Centre — and come paint the Mcintyre bluff for the holidays!

All levels welcomeSnacks & tea includedTake home your masterpiece

Limited seats — reserve yours early and come paint the valley you love!

Sign up at the Visitors Centre or call 778-439-2363

Mingle & Jingle
2025-12-11 19:00 - 21:00 | Stella & Rose, 8313 Main St #104, Osoyoos, bc, V0H 1V0, Canada

Public Skate
2025-12-12 08:00 - 17:00, 2025-12-13 08:00 - 17:00, 2025-12-14 08:00 - 17:00 | District Wine Village, 100 Enterprise Way British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Friday’s Public FREE Skate | 12:00pm – 5:00pmSaturday’s Public FREE Skate | 12:00pm – 5:00pmSunday’s Public FREE Skate | 12:00pm – 5:00pm

Monday – Thursday | Private group skating bookings available

RINK CLOSEDDecember 23 – 26 & January 1 – 2

Skate Rentals | $5 per personSkate Sharpening | $5 per pair

*No Shoes/Boots on Skating Surface*Skates only

Skate Sharpening | $5 per pair | **available Thursday’s & Friday’s**

Ladies Keep Fit
2025-12-12 08:30 | Oliver Senior Centre, 5876 Airport Street British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Join in the fun all December long at the Olivers Senior Centre

Winter Wonderland
2025-12-12 12:00 - 17:00, 2025-12-13 12:00 - 17:00, 2025-12-14 12:00 - 17:00 | La Stella Winery, 8123 148 AVE, Osoyoos, BC, V0H 1V2, Canada
Step into a Magical Advent-Calendar celebration at La Stella Winery.

24 days of wine, art, and community cheer!

Each day brings something new: a winter display created by a local community group, a tasting of a specially selected wine from La Stella or Le Vieux Pin, and a local Artisan pop-up with one-of-a-kind gifts.

Tasting fees and a portion of sales help support participating community groups.

December 1: Osoyoos Festival SocietyDecember 2: Oliver & Osoyoos Search & RescueDecember 3: Osoyoos Lake Paddling ClubDecember 4: Oosoyoos Desert CentreDecember 5: Oliver & Osoyoos Desert Sun CounsellingDecember 6: Anarchaist Mountain Fire DepartmentDecember 7: Oosyoos Activity CentreDecember 8: Oliver Food BankDecember 9: South Okanagan Skating ClubDecember 10: Osoyoos Museum SocietyDecember 11: Oliver Heritage SocietyDecember 12: Oosyoos Food BankDecember 13: Oosyoos Fire & RescueDecember 14: Osoyoos Activity CentreDecember 15: Oliver Mission SocietyDecember 16: Desert Pickleball ClubDecember 17: Oliver Curling ClubDecember 18: Oosyoos Curling ClubDecember 19: Oosyoos Lawn Bowling ClubDecember 20: Oosyoos Day CareDecember 21: Oliver & District Fire Department December 22: Oosyoos Music in the ParkDecember 24: Oosyoos Lake Sailing ClubDecember 25: Oosyoos Lake Water Quality Society

WIPIZZA
2025-12-12 12:00 - 22:00, 2025-12-13 12:00 - 22:00, 2025-12-14 12:00 - 22:00 | Miradoro Restaurant, 537 Tinhorn Creek Rd. British Columbia Oliver V0H 1T1 Canada, Oliver, British Columbia, V0H 1T1, Canada
WIPZZA!

Buy a bottle of wine & get a free pizza!

Dine in only.

No further discounts and not in combination with another offer.

Regular menu, up to 10 guests.

Bingo
2025-12-12 13:00 | Oliver Senior Centre, 5876 Airport Street British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Join in the fun all December at the Oliver’s Senior Centre

Rise Dance Academy Presents - A Cozy Christmas Showcase
2025-12-12 18:00 - 19:00 | Rise Dance Academy, 6237 Main St, Oliver, BC, Canada
Let the dancers of Rise Dance Academy awe and entertain you with a holiday program full of cozy classics and festive charm. This heartwarming showcase brings together students of all ages as they share the joy, nostalgia, and magic of the season through movement and music. It’s a chance to settle in, soak up the spirit of the holidays, and enjoy an afternoon that feels familiar and fresh at the same time.​Before the show, you’ll find baked goods and thoughtful handmade items for sale, with all proceeds supporting the Oliver Competitive Dance Society. It’s a simple way to treat yourself, pick up a small gift, and cheer on young dancers who are working hard to follow their passion. A lovely way to kick off the season with family, friends, and community.

TICKETS: Adults – $30, Seniors – $20, Kids (3-18) – $10

Paint, Sip & Savour | Ticket
2025-12-12 18:00 - 20:00 | River Stone Estate Winery, 143 Buchanan Drive British Columbia Oliver V0H 1T2 Canada, Oliver, British Columbia, V0H 1T2, Canada
Paint, Sip & Savour in the Cellar at River Stone Estate Winery

Join us for a creative evening in our cellar! River Stone’s very own Aidaan Gaudet—tasting room associate by day and talented landscape artist by night—will guide you step-by-step through painting your own masterpiece.

🌿 Friday, December 12th🕕 6PM | River Stone Estate Winery, Oliver

🎟 Tickets: $55+tax | Club Price: $50+tax (Limit 2)

Includes all painting supplies, a glass of our award-winning wine, and a selection of charcuterie bites.

Limited spots available.

Gingerbread Cookie Decorating
2025-12-12 19:00 | See Ya Later Ranch, 2575 Green Lake Road British Columbia Okanagan Falls V0H 1R0 Canada, Okanagan Falls, British Columbia, V0H 1R0, Canada
Bring the whole family for a fun and festive gingerbread decorating workshop! Make sweet memories (and even sweeter treats) this holiday season.Your ticket includes:🍷 A glass of See Ya Later Ranch wine for adults🧀 A delicious charcuterie spread🍪 All cookie decorating materials & guidanceLimited spots—reserve today for a deliciously festive experience!💲 $40 per adult | free kids (up to 2 children per paid adult)

Oliver Handbell Ringers Presents " Bethlehem Night"
2025-12-12 19:30 | Osoyoos Baptist Church, 6210 97th Street British Columbia Osoyoos V0H 1V4 Canada, Osoyoos, British Columbia, V0H 1V4, Canada
The Oliver Handbell Ringers & Their Singers present their annual Christmas concert, “Bethlehem Night.”

Experience the pure joy and incredible music of the Nativity story, celebrating the promise fulfilled and the light in the darkness through the unique, uplifting sound of a community choir blended with handbells. This is a very special gift to our community this holiday season.

Performances are Friday, December 12 at 7:30 PM and Sunday, December 14 at 3:00 PM at Osoyoos Baptist Church (6210 Highway 97). Admission is free (donations welcome).

Dance Live Band
2025-12-13 10:00 | Oliver Senior Centre, 5876 Airport Street British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada

Terroir of Chocolate and Coffee Workshop
2025-12-13 10:00 - 12:00 | District Wine Village, 100 Enterprise Way British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Join us for a long table workshop to learn about the terroir of chocolate and coffee with local Sommelier & Chef, Rachelle Goudreau.

Rachelle will guide each of the participants in the tasting experience which includes ten chocolate tastings and four different coffees supplied by local roaster, Wolftree Coffee Co.Rachelle will explain the different factors that influence the flavour and how to pair the chocolate with coffee & wine to bring out the best flavour experience.

Everyone will also go home with a printed guide on Terroir of Chocolate and Coffee, as well as a 500 piece galison foil chocolate puzzle from Gather Books & Lovely Things.Wolftree Coffee Co. will be offering 10% off their giftware and Gather Books will be offereing 10% on all books and gifts that morning.

Merry Morsels
2025-12-13 12:00, 2025-12-14 08:00 - 17:00 | Cellar Door & more, 7857 TucElNuit Drive British Columbia Oliver V0H 1T2 Canada, Oliver, British Columbia, V0H 1T2, Canada
Merry Morsels – December 13–14Sweeten your holiday shopping at Merry Morsels! Indulge in seasonal favourites from Purdy’s Chocolates while you explore exclusive in-store savings on your favourite wines. It’s a delicious way to treat yourself while checking off your holiday list.

And the best part? With every purchase, you’ll get to pick a Purdy’s chocolate bar to take home—a little extra sweetness to make your day merry and bright!

Holiday Open House at Phantom Creek Estates
2025-12-13 12:00 - 16:00 | Phantom Creek Estates, 4315 Black Sage Road British Columbia Oliver Canada, Oliver, British Columbia, Canada
Details:

Join us for a festive afternoon at the winery as we celebrate the season with our Holiday Open House.

Tickets are free! Quantities are limited.RSVP via the tickets link below.

Enjoy complimentary mulled wine, Christmas cookies, and a curated charcuterie selection while exploring the winery at your own pace.

Frozen eggnog, along with wine by the glass or bottle, will be available for purchase. Gather your friends and family for a cozy, cheerful kickoff to the holidays.

There will be puzzles and board games to enjoy while you sip on wine and enjoy some snacks. At our craft station, you can create your own card with our holiday stamps and art supplies.

This event will take place in the Phantom Creek Estates Tasting Room. We look forward to welcoming you!

Link for tickets: https://www.exploretock.com/phantomcreekestates/event/582346/holiday-open-house

A Very RUSTY Christmas
2025-12-13 13:00 - 16:00 | Rust Wine, 4444 Golden Mile Bench British Columbia Oliver V0H 1T1 Canada, Oliver, British Columbia, V0H 1T1, Canada
We cant wait to celebrate the holidays with you! We are thrilled to welcome back the wonderful Lewis Cardinal for a cozy afternoon filled with LIVE music, warm mulled wine, and delicious bites crafted by the incredibly talented Andre. And of course, there will be plenty of Rust vino – whether you prefer a glass or a bottle!

Here are the festive details:Date: Saturday, December 13thTime: 1:00pm to 4:00pm-ishNo cover, no entry fee. Just bring your favorite holiday pals and come soak up some seasonal magic with us among the vineyards of the Golden Mile Bench.

We can’t wait to celebrate with you!

1st Annual Village Chritmas Party
2025-12-13 14:00 - 18:00 | District Wine Village, 100 Enterprise Way British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
You’re Invited to our 1st Annual Village Christmas Party!

Bring your colleagues, friends, and family to celebrate before the holidays at our 1st Annual Village Christmas Party.

What’s Happening• Wear your ugly Christmas sweater• Live music with Mandy Cole• Free skating and a visit from Santa (and maybe the Grinch)• Last‑minute gift ideas from small local businesses• Door prizes — bring a non perishable food item to donate towards the Christmas Food Hampers and recieve an extra entry for every donation

Join us to spread cheer and support our community.

Happy holidays!

Jingle Ball
2025-12-13 18:00 | Watermark Beach Resort, 15 Park Pl, Osoyoos, BC, V0H 1T0, Canada
Get ready for an unforgettable evening at the Watermark Jingle Ball on Saturday, December 13th. The event kicks off at 6 PM with a glass of bubbly and passed canapés, setting the perfect mood for a night of holiday cheer.

Enjoy a gourmet seasonal buffet, capture a photo with Santa and then dance the night away to tunes from our local DJ.

Tickets are $89 per person (plus taxes & service).

To reserve your spot, please contact us at sales@watermarkbeachresort.com, call 250-495-5511, or visit our website.

Music Bingo
2025-12-13 18:30 | Backroads Brewing, 15 Park Pl Unit 226, Osoyoos, bc, V0H 1V0, Canada
A fantastic evening of good tunes, great beer, and fun times.

Gather Oliver - Storytime with Alaina
2025-12-14 11:00 - 11:30 | District Wine Village, 100 Enterprise Way British Columbia Oliver V0H 1T0 Canada, Oliver, British Columbia, V0H 1T0, Canada
Join us for a free drop in story time every week. All ages are welcome!

Follow along on Instagram, for other family friendly events.

Holiday Market | Red Barn Winery
2025-12-14 11:00 - 15:00 | Red Barn Winery at Jagged Rock, 4305 Black Sage Road British Columbia Oliver V0H 1T5 Canada, Oliver, British Columbia, V0H 1T5, Canada
We’re making holiday shopping a little more fun this year by doing something we’ve never done before.

Our first holiday market at Red Barn!

Drop in for an easygoing afternoon of live music, local wine vendors, gourmet hot dogs, Red Barn tastings at special event pricing, and holiday wine shopping, including our limited Cabernet Franc.

A rare library release available for four hours only, typically reserved for members. Plus, expect a few more surprises to be revealed at the event.

Sunkeya Farm Alpacas | Open House
2025-12-14 11:00 - 15:00 | Sunkeya Farm Alpacas, 1264 Green Lake Road British Columbia Oliver Canada, Oliver, British Columbia, Canada
