Your 2026 Guide to Romance, Fun, & Heartfelt Memories
Valentine’s Day is a chance to slow down, share meaningful moments with the people who matter most, and create memories that will last a lifetime. Here in Simcoe County there are plenty of ways to celebrate love in all its forms. From cozy to playful, heartfelt to unexpected, this year invites you to skip the predictable and discover local experiences that make the day feel special in all the right ways.
Cozy Winter Romance & Outdoor Adventures
If your idea of romance includes fresh air, twinkling lights, and winter magic, these experiences set the mood perfectly.
Take in the magical forested skate trail at Simcoe County Museum’s “Skate & Sweets” event. Warm up with a cup of hot chocolate, indulge in sweet treats, and play a few games. Then capture festive photos that will keep the memories alive long after the ice has melted.
Sometimes the best plans involve slowing down, and a day at the Vettä Nordic Spa in Oro-Medonte offers exactly that. Surrounded by nature, you’ll experience the restorative power of authentic Finnish hydrotherapy. After, enjoy a nourishing meal at the on-site bistro or fine dining restaurant. Whether you’re escaping with your partner or taking time for yourself, it’s a peaceful, rejuvenating way to spend the day.
For a truly enchanting experience, head to Snow Valley Ski Resort for the Torchlit Snowshoe Hike. More than 200 torches illuminate a 2.6 km forest trail, casting a warm glow through the snowy woods. Halfway through, cuddle up by a crackling campfire with complimentary snacks and drinks while taking in the quiet beauty of winter.
At Friday Harbour, the “Friday, I’m in Love” Skate Escape transforms the promenade into a full day celebration. Enjoy free skating on a red-lit rink, DJ sets, live performances, romantic vow renewals, vendors, and themed photo ops. In between laps, warm up in the cozy après-skate lounge, then wrap up the day with a romantic dinner at the Lake Club. You can also browse the promenade’s boutique shops for the perfect Valentine’s find.
Date Night with a Punchline
Nothing brings people together quite like shared laughter, and Simcoe County has no shortage of comedy this Valentine’s Day.
“Roses Are Red, Comedy Is Better” brings Yuk Yuk’s touring show to CW Coops in Barrie, featuring headliner Eric Andrews. Grab some wings, settle in, and let the laughs set the tone for the night.
At Taps and Tunes Bar & Grill in Collingwood, The Ava Val-entine’s Comedy Special stars John Candy Award-winning comedian Ava Val. They will be serving up a show filled with humour, love, and heartwarming laughs.
Classic Romantic Dinners
If a timeless night out is what you’re after, these intimate dining experiences offer the perfect setting. Check out these options for great food, good conversation, and meaningful connection.
For an elegant evening, try Oliver & Bonacini CafĂ© Grill in Collingwood. Their Valentine’s Day special sets the mood with a three-course menu, complimentary Prosecco, and handcrafted cocktails. Whether you’re toasting with a partner, celebrating with friends, or winding down after a day on the slopes, it’s a stylish way to mark the occasion.
For a dose of timeless romance, Il Buco in the heart of Barrie is unmatched. Recognized by OpenTable as one of Canada’s 100 Most Romantic Restaurants, it delivers nostalgic cuisine in a warm, intimate setting. Just steps from Kempenfelt Bay, it’s a beautiful spot to savour dinner and follow it up with a peaceful boardwalk stroll by the water.
Drink & dine with a twist
Donaleigh’s Irish Pub in Barrie is turning up the fun with their Valentine’s Day Dine & Dance event. A thoughtfully curated five-course dinner will be followed by dancing and live music by The Thunderstealers. It’s the perfect mix of great food, lively atmosphere, and feel-good entertainment to make your date night one to remember.
Pier 21 Restaurant & Bar in Penetanguishene invites couples to “Eat Your Heart Out” this Valentine’s Day, with a special menu, a celebratory champagne toast, and live entertainment setting the tone for a relaxed, intimate evening. For those who prefer a quieter atmosphere, the earlier 3:30 p.m. seating offers pre-peak pricing – perfect for couples looking to enjoy a cozy dinner before the evening crowd rolls in.
Cocktail lovers can stir up some fun at the Cottage Country Cocktails Workshop hosted by LVX Beauty Lounge in Barrie. This interactive experience includes hands-on instruction to craft three signature drinks, playful themed games, and plenty of laughs – plus, you’ll leave with new mixology skills perfect for future date nights.
Unique Dates & Hands on Experiences
Looking for something memorable and a little different? These experiences invite curiosity and connection.
The Orillia Leacock Museum puts a hauntingly romantic twist on Valentine’s Day with “Love Never Dies: A Ghostly Valentine’s Event”, a playful blend of eerie and enchanting. Start the evening with a guided “paint your partner” workshop and psychic love readings. Then take in a curated exhibit of ghostly love stories, and a complimentary drink to sip while you explore the museum.
Take things onto the dance floor at Innisfil’s Lakeside Dance with “Sway Into Romance”, a Valentine’s-themed evening centered around the Rumba – often called the dance of love. Perfect for beginners, the night includes a relaxed dance lesson, a glass of wine, hand-dipped chocolate strawberries, and the warmth of a cozy fireplace to set the mood.
For a night full of playful energy, head to the Barrie Rec Room. Arcade games, bowling, great food, and drinks set the stage for hours of fun. Looking for a group option? The Valentine’s Double Date Package at Bullseye Axe Throwing brings the excitement with interactive projector targets, themed games, included drinks, and popcorn, promising an action-packed night out with friends.
Get Creative With Your Partner
Add a playful twist to date night with activities that let you get creative together.
At Debut Bar & Restaurant in Barrie, their Valentine’s Paint Night offers a fun and relaxed way to connect – no experience needed. Sip, snack, and let your creativity flow as you paint a keepsake masterpiece to take home, making it a date night to remember.
If pottery is more your style, the Valentine’s Vibes Party at The Paint Bar in Wasaga Beach lets you get cozy, create, and connect as you paint a pottery piece of your choice. With a complimentary mocktail and a charcuterie box included, it’s a hands-on date that’s sure to leave a lasting impression.
Art lovers can find inspiration at the opening night reception of “Spirit Beads”: The Paintings of Patti Belanger at the Midland Cultural Centre’s Gallery of Indigenous Art. Showcasing a vibrant fusion of contemporary pointillism, mixed media, and beadwork rooted in MĂ©tis heritage and the natural beauty of Georgian Bay, Belanger’s work offers a meaningful, visually rich experience – perfect for a thoughtful and inspiring date night.
Theatre & Live Performance Events
Celebrate the magic of live performance this Valentine’s Day. Captivating storytelling, moving music, and unforgettable moments set the stage for a truly memorable night.
The Mariposa Arts Theatre brings WROL (Without Rule of Law) to the stage at the Orillia Opera House. This production is a bold and thought-provoking production that follows a group of preteen “doomers” preparing for a world they no longer trust. With its sharp perspective and emotional depth, it offers a fresh and impactful take on a night out.
At The Historic Gayety Theatre in Collingwood, First Date: A Musical Comedy serves up laugh-out-loud moments with a witty take on modern dating. Complete with awkward first impressions, unexpected twists, and hilariously honest inner monologues. It’s a fun and relatable pick for couples who enjoy a good laugh and a lively night of theatre.
For music lovers, Valentine’s Day meets Black History Month at Barrie’s Five Points Theatre with an unforgettable performance by Maestro Fresh Wes. Hosted by the AfroCaribbean Multicultural Association, this dynamic evening celebrates love, culture, and the legacy of Canadian hip hop, with food options available to round out the experience.
Family Friendly Activities
Valentine’s Day is also a great excuse for a little family fun, with plenty of local events that let you celebrate love and togetherness with the kids in tow.
The annual Wasaga Beach SnowmanMania Winter Festival brings the community to life with a weekend full of family-friendly fun. Including crafts, games, skating, snow-filled activities, and live performances, there is something for everyone to enjoy. It’s a lively way to celebrate the season and add some Valentine’s weekend excitement with the whole family.
The Orillia Museum of Art & History invites families to A Victorian Family Valentine, a free drop-in event where you can create old-fashioned valentines together in a cozy and welcoming setting – perfect for slowing down and sharing a little hands-on fun.
Discovery Harbour’s annual Mid-Winter Social turns its historic grounds into a charming winter celebration. Complete with wagon rides, snowshoeing, tubing, firepits, heritage demonstrations, live entertainment, warm treats, artisan vendors, and more. It’s a festive, family-friendly way to embrace the season while learning some local history.
Celebrate Love Your Way in Simcoe County
Whether you’re planning a romantic date night, a fun outing with friends, quality time with family, or a well deserved day for yourself, love is in the air all across Simcoe County. Choose what feels right, embrace the moment, and make this Valentine’s Day one to remember!
