Monday January 26, 2026 to Sunday February 15
Valentine’s Day Guide
Valentineโs Day is the perfect excuse to slow down, reconnect, and treat someone special. Whether youโre planning an intimate candlelit dinner, a cozy night out, or a full day of memorable experiences, Windsor Essex offers no shortage of ways to celebrate love.
From romantic dining spots and charming local wineries to unique date ideas and indulgent experiences, this guide highlights the best romantic dinners and things to do to help you plan a Valentineโs Day that feels effortless, meaningful, and unforgettable.
Design your own Custom Valentine’s Day Wine label at cooper’s hawk vineyard
January 20th – February 12th. Online only.
This Valentineโs Day, your wine comes with a little extra love! Design your own custom wine labelโchoose from 5 sayings or upload a photo of you & your Valentine.
Bonus: Each order includes a chocolate treat fromย Dutch Boys Chocolate and a set of wine charms.
Cooper’s Hawk Vineyards
1425 ller Rd, Harrow
Event Listing
Limited Edition Valentine’s Day Popcorn at What’s poppin’ย
Get ready for Valentine’s Day with our Lovestruck pink and red kettlecorn. Single serving bags are perfect for a little addition to a box of chocolates or diamonds! We are ready when you are to make your loved ones happy.
What’s Poppin’ Popcorn Factory
5320 Brendan Ln, Tecumseh
Limited Edition Popcorn
Valentine’s Day Sip & bedazzle night
February 6th at 7:00pm
We’re back with another Sip & Bedazzle night! We had so much fun last time – we decided to do it again! If you missed out last time, come join us for a Valentine’s themed night with your friends! We will provide the gems & the snacks & the drinks – you bring your book and your friends!
$25 + tax per person. Message for payment details and to reserve your spot! We will sell out fast.
Fiona’s Book Corner
575 Notre Dame St, Belle River
Event Listing
Love is in the air
February 8th from 10:00am.
A Valentineโs Day Market is a charming pop-up shopping experience filled with handmade gifts, cozy treats, and all things heart-themed. Vendors showcase unique crafts, jewelry, dรฉcor, and goodies perfect for celebrating loveโwhether itโs romantic, family, friendship, or just treating yourself (the most reliable Valentine of all).
FREE ADMISSION EVENT PRESENTED BY: Romaโs Crafty Creations ONLY
Fogolar Furlan Club
1800 North Service Road, Windsor
the pop yard – love edition
February 8th from 10:00am until 3:00pm
The Pop Yard Love Edition! Local makers, vintage, crafts & treats. Feb 8, 10amโ3pm. Royal Canadian Legion 644, Windsor. Free entry.
A Valentineโs Day pop-up market with vintage, crafts, brand-new items, local & small businesses, services, and homemade treats & snacks. Itโs Super Bowl Sunday โ the bar will be open! Come shop, enjoy the atmosphere, and grab snacks for your Super Bowl night. Free entry & parking!
Royal Canadian Legion Branch 644
1570 Marentette Ave, Windsor
Event Listing
Galentine’s Day Vibes, Vision boards & Vino
February 12th from 6:00pm until 8:00pm
This Galentineโs Day, join us at Lakeshore Lodge for a fun, feel-good night designed around connection, creativity, and elevated vibes! This experience is all about bringing women together in a relaxed, inspiring space to unwind, laugh, and create โ no pressure, no expectations, just a beautiful evening with great energy!
Weโll begin with a gentle guided meditation to help you relax, settle in, and shift out of the busy energy of the day. From there, youโll move into a fun creative activity to get the ideas flowing and tap into what you want more of in your life this year.
Once youโre feeling inspired, youโll bring it all to life by creating your own vision board on canvas โ playful, personal, and something youโll love taking home. Your ticket includes one glass of wine to sip and enjoy as you create (feel free to bring your own).
Expect wine, laughter, meaningful connection, and creativity โ the kind of night that feels lighthearted, uplifting, and exactly what you need. This is a celebration of friendship, self-expression, and doing something just for you.
$55 per person.
The Lodge at Lakeshore
1258 County Rd 22, Emeryville
Event Listing
Galentine’s Dayย at Walkerville Brewery
February 12th 6:00pm
Paint Your Ride or Die – Besties, Beer & Brushes The taproom will be buzzing with fun workshops and pop-ups from incredible women-owned local businesses, plus special features from the brewery. Weโll be there with our Paint Your Ride or Die pottery experience where youโll paint a custom portrait of your Ride or Die bestie (or your fur bestie!) on your choice of a mug or plate, using our foolproof tracing technique.
No art experience needed. This is one of our most-loved workshopsโnow paired with drinks and brewery vibes! Space is limited, so grab your ticket and come create something youโll treasure.
Walkerville Brewery
525 Argyle Rd, Windsor
Event Listing
Paint your palย ย
February 12th 6:30pm
Celebrate Galentine’s Day early with friendship and a paintbrush in hand!
Grab your bestie, take a seat across from one another, and create a fun, quirky portrait that captures their personality.
This upbeat, laugh-out-loud paint session is all about creativity, connection, and not taking things too seriously.
Tickets: $90 + tax
Ticket price includes:
* Two (2) workshop tickets,
* Supplies
* A Charcuterie snack box for 2
* Two (2) Sparkling wine sample upon arrival
Expect bright colours, inside jokes on canvas, and a hilarious keepsake youโll treasure long after Galentineโs Day.
Coopers Hawk
1425 Iler Rd, Harrow,
Event Listing
Love & Clay Sip, Spin, and Spark Romance
February 12th to February 14th
Celebrate Valentineโs Day with a playful, hands-on pottery experience made for couples.
Spend the evening laughing, creating, and connecting as couples games and lighthearted activities are mixed throughout a guided pottery wheel session. The experience is designed to keep things fun, interactive, and relaxedโno pressure, no awkward moments, just good energy.
Expect a cozy, romantic studio vibe with great music, plus wine and refreshing beverages included to keep things flowing as you shape clay side-by-side and create something truly one-of-a-kind together. This night is less about perfection and more about connection, creativity, and sharing an experience youโll actually remember.
And yes โ there will be plenty of photo-worthy momentsโฆ including your very own iconic โGhostโ scene. Event Includes: Snacks, wine, beer, cocktails, fun dating games + more
Sketch Clay + Pottery
55 E Pike Creek Rd, Tecumseh
Event Listing
Steak and date night at sawyers craft bbq
February 13th and 14th.
Steak & Date Night is back, and making its first appearance of the new year just in time for Valentineโs Day, and weโre going BACK to BACK NIGHTS! Friday February 13th & Saturday February 14th we will be offering three seating times at 5:00pm, 7:00pm, and 9:00pm for each date.
LIMITED SEATING. RESERVATIONS ONLY
$125 Per Couple
- Proteins: 24oz Dry Aged Canadian Prime Ribeye served With Roasted Garlic & Marrow Herb Butter, Filet Mignon Duo with Peppercorn Cream or King Crab Oscar Sauce (Add $20), Rack of lamb with Pomegranate Molasses or Upgrade to 30oz Dry Aged Wagyu Porterhouse
- Sidess: Grilled Cesar Salad, Tallowโd Roasted Fingerlings, Stout Battered Onion Rings, The Brussels Sprouts, Truffle Mac & Cheese (Add $5), Oysters on the half shell with, Passion Fruit Mignonette, Classic Prawn Cocktail or Loaded Crab Claw Cakes
- Choice of dessert will be crafted by @thepantrybakeshop
To Book, please call 519-252-5455, DM or email us at [email protected]
Sawyers Craft BBQ
1000 Drouillard Rd, Windsor
Event Listing
Valentine’s Day at Cooper’s Hawk Vineyardsย
February 13th – 14th.
Be mine at The Vines!
Because the best pairing isn’t just food and wine — it’s who you share it with.
Call us to reserve your table 519.738.4295 (Press ‘3’ for The Vines)
Cooper’s Hawk Vineyards
1425 Iler Rd, Harrow
Menu
Valentine’s Day at Cured craft brewing co.ย
February 13th – 14th.
Let us take care of you and your loved one with a nice evening out for Valentine’s. Reserve your spot on February 13th and 14th to enjoy a special Valentine’s menu in addition to our regular menu. We will have:
- Beef Bourguginon
- Chicken Parmesan
- Pasta Primavera
End your evening with our vanilla bean cheesecake for dessert. Limited availability.
Reserve your table by calling (519)419-3822
Cured Craft Brewing Co.
43 Mill St W, Leamington
Menu
Valentine’s Day at gladstone commons
February 13th – 15th.
We will be featuring a 4 course Loverโs Prix Fixe for you and that special someone! Spots have filled up very quickly for the 14th, so we wanted to spread the love and announce we will be running out Valentineโs Day menu on from the 13th to the 15th.
Reservations are available now so book your table before itโs gone!
Gladstone Commons
792 Gladstone Ave, Windsor
Menu
Valentine’s Day at hyatt Place Windsor
February 13th – 15th.
Valentine’s Day Package:
- Late Checkout at 2:00pm
- Lounge in luxurious robe and slippers during your stay!
- The Placery food credit $10 (Valid only on February 14th, 2026.
Hyatt Place Windsor
2080 Huron Church Rd, Windsor
Special Offer
Valentine’s Day at North 42 Degrees Estate Winery
February 13th and 14th.
A Romantic Evening Awaits This Valentineโs Day at North 42! The scene is set: a cozy restaurant, a burning fire, soft romantic music, flickering candlelight, and a delightful swirl of spaghetti.
Join us in celebrating your love this Valentineโs Day, Friday, February 13th or Saturday, February 14th. Indulge in our classic dinner feature of spaghetti and meatballs, made timeless by those romantic dogs in Disneyโs Lady and the Tramp, or select from our regular menu options all made with love.
Reservations are now available. Call 519-738-6111 to book your table today!
North 42 Degrees Estate Winery
130 Essex County Rd 50, Harrow
Event Listing
Love Hurts Valentine’s Pop-up at windsoreats
February 13th from 5:00pm until 11:00pm
This Friday, February 13, weโre leaning all the way into the chaos with LOVE HURTS at WindsorEats Food Hall โ and yes, itโs FREE to attend. Whether youโre coupled up, freshly single, or emotionally unavailable but thriving, this night is for you.
Whatโs going down:
- Real tattoos from a live tattoo artist (actual ink, real commitment)
- Live folk + banjo music by Folk Around And Find Out bringing the perfect moody soundtrack
- Valentineโs-themed drinks (sweet, spicy, and a little unhinged)
- Food trucks to keep you fed and happy
- Come get inked, sip something pink, scream-sing to folk music, and embrace the messiness of love โ or the lack of it.Bring a date, bring your friends, or roll in solo and leave with a tattoo and a story.
WindsorEats
400 Erie St E Unit 3, Windsor
Event Listing
Galentine’s Night at Walkerville Brewery
February 13th from 6:00pm until 9:00pm
Calling all gal pals! Grab your besties and join us for the ultimate girl gang hangout!
Galentineโs at the Brewery is happening on Thursday, February 13th from 6-9PM! Weโll be featuring fun workshops and pop-ups from amazing women owned businesses plus fun taproom features.
Activities + features include:
- Sip and paint with Sip Nโ Swirl
- Get permanent jewelry with your besties by AloraFlora
- Friendship Bracelet Making with AloraFlora – Drop-in activity; $5 per person
- Candle making workshop with Flakes & Flames
- Valentine cookie decorating with Sunset Sweets – Drop in activity; purchase your cookie kits ($22.50) on site!
- Treat yourself and shop with Birk Boutique
- Fun photobooth pop-up compliments of BloomLux Walls
- Enjoy drink + snack features in the taproom
You donโt need to be taking part in the activities to come hangout with your gal pals, everyoneโs invited!
Walkerville Brewery
525 Argyle Rd, Windsor
Event Listing
Galentine’s Day at November’s Eve
February 13th at 7:00pm
Looking for something fun to do with your friends this Valentineโs Day? We are hosting a Galentineโs Day event you donโt want to miss! Join us on February 13th @ 7pm sharp for an exclusive event!
Tickets include :
- Snacks & Treats
- Lip Balm Keychain & 3 Charms
- Two Tapered Candles & Paint
- Ribbon to decorate
- Exclusive discounts & a private shopping experience
- Games & Prizes
- Good vibes & company
Tickets: $60
November’s Eve
100 Lesperance Rd Unit 2, Tecumseh
Event Listing
Valentine’s POP up at Urban Art Market
February 13th to February 14th – 11am to 6pm
Come celebrate Valentineโs weekend with us and a bunch of amazing local makers!ย Along with all the great handmade Valentineโs gifts already in the shop, weโre hosting a special Valentineโs POP-UP in our studio on Friday Feb 13 & Saturday Feb 14 (11โ6). Youโll find sweet treats, pottery, and handmade goods โ perfect for gifting (or treating yourself).
Makers popping up:
โข WhiskingBabe โ sweet treats (Fri/Sat)
โข Danielle Whitney Handmade (Fri/Sat)
โข Whimsy Brooke (Friday)
โข Tayโs Clays (Saturday)
โข Pottery by Teri (Saturday)
Shop local, find something special, and spend part of your Valentineโs weekend with us
Urban Art Market
548 Chilver Rd, Windsor
Event Listing
Valentine’s Day at koolini’s
February 14th.
Takeout.
Valentineโs Day specials are up! There are two options available so make sure you call today and place your order!
1520 Tecumseh Rd E, Windsor
Menu
Prix Fixe Dining Experience at Kingscoast Estate Winery
February 14th.
Weโre thrilled to invite you to celebrate our very first official Valentineโs Day with a special prix fixe dining experience at Kingscoast Estate Winery! Join us in the Brix Tasting Lounge for an unforgettable evening of thoughtfully curated cuisine, fine wine, live music and romantic ambiance.
Limited seating is available – reservations only to secure your table.
Kingscoast Estate Winery
1000 McCain Side Rd, Kingsville
Menu
Valentine’s Day at River Room Resturant
February 14th.
Valentineโs Day is just around the corner! Book your table now at River Room Restaurant! Stay tuned as weโll be sharing more details about our special features, alongside our main menu and live music!
River Room Resturant
277 Riverside Dr W, Windsor
Event Listing
Valentine’s Cocktail Class
February 14th from 11:00am – 1:00pm
Love a good cocktail? Learn to be a mixologist and to make bar-worthy cocktails with and for your love!
Get ready to raise a glass because WindsorEats is bringing back Be A: Mixologist, part of our exciting series of hands-on classes (including fan-favourites like Be A: Sausage Maker). This time, we’re shining the spotlight on the finest whiskies made right here in town! For just $80 per person, youโll dive into the world of craft cocktails with expert guidance, hands-on learning, and, of course, some top-notch sipping.ย Whatโs in Store?
- Sip & Learn: Kick things off with a perfectly crafted welcome cocktail.
- Interactive & Fun: This isnโt a boring lectureโget hands-on and shake things up in a lively, engaging atmosphere.
- Expert-Led Mixing: Our mixologists will guide you through the art of creating three different whisky cocktails using various techniques.
WindsorEats
400 Erie St, Windsor
Event Listing
Valentine’s Wine, Cheese and Chocolate from muscedere
February 14th at 1:00pm
Indulge in a thoughtfully curated sensory experience at Muscedere Vineyards with your Galentine or loved one. While weโve previously hosted at The Cheese Bar, weโre delighted to welcome you to the vineyard for this special tasting on Saturday, February 14th, 2026 at 1pm. Enjoy a one-hour guided tasting featuring four Muscedere Vineyards wines, each expertly paired with a selection of handcrafted artisan cheeses and chocolate.
Your tasting will be hosted by Melissa of Muscedere Vineyards alongside Sarah of The Cheese Bar.
Tasting Includes
-4 Muscedere Wine Samples
-4 types of Cheese and Chocolate and small accompaniments
-Tasting Notes/Pairing Suggestions
-1 hour guided tasting with Melissa of Muscedere Vineyards and Sarah Barrette of The Cheese Bar
Muscedere Vineyards
7457 County Rd 18, Harrow
Buy Now!ย
weekends in the studio – Valentine’s Day Card with Meaghan Sweeney
February 14th Drop in from 1:00 pm – 4:00 pm
In the studio this week, artist Meaghan Sweeney will show you how to make an expressive card for your loved one. Show your appreciation this Valentines with a handmade card.
This program is free with admission to AWE and open to all.
Art Windsor Essex
401 Riverside Dr. W, Windsor
Event Listing
paint your partner workshop – Cooper’s hawk vineyard
February 14th at 2:00pm
Put a creative twist on Valentineโs Day and paint the one you love!
Sit face-to-face with your partner and turn them into your artistic inspiration in this relaxed, romantic-meets-playful experience.
No painting skills neededโjust a willingness to have fun together.
Tickets: $90 + taxย OR 519.738.4295 ‘Retail’
Ticket price includes:
- Two (2) workshop tickets
- Supplies
- A Charcuterie snack box for 2
- Two (2) Sparkling wine sample upon arrival
Leave with a heartfelt (and possibly hilarious) portrait and a memorable Valentineโs Day moment to take home.
Cooper’s Hawk Vineyard
1425 Iler Rd, Harrow
Event Listing
Valentine’s day at nico walkerville
February 14th from 5:00pm – 9:30pm
- Early seating: 5:00pm, 5:15pm and 5:30pm $100 per person
- Prime seating: 7:00pm, 7:15pm and 7:30pm $120 per person
- Late seating: 9:00pm, 9:15pm and 9:30pm $100 per person
Two hour dining time & menu. (Menu subject to change.)
- Starters: Hamachi Crudo, Arugula Salad, Beef Tartare, Tempura Mushroom or Shrimp Fra Diavola
- Pastas: Gnocchi Gorgonzola, Gnocchi Spicy Vodka Blush, Rigatoni Al Brasato, Ziti Al Ragu Di Polpette or Roasted Butternut Squash Risotto
- Entrees: Lamb Rack, Glazed Roasted Chicken, Braised Short Rib, Steelhead Trout or Roasted Root Vegtables-Lemon Tarragon Bearnaise
Reserve Onlineย Here. Prices do not include beverages, tax or 20% gratuity.
Nico’s Walkerville
501 Erie St E, Windsor
Menu
Valentine’s day at Paglione estate winery
February 14th at 5:00pm and 8:00pm
This Valentine’s Day, escape to the heart of wine country with us for an unforgettable wine pairing dinner experience. Whether you’re celebrating with someone special, gathering with friends, or simply treating yourself to something indulgent, this candlelit dinner offers a warm and intimate setting to enjoy a thoughtfully curated culinary journey. Romance the night, celebrate family or friendship, or simply treat yourself with a 4-course candlelit wine pairing dinner.
- $105 per guest includes Josephine Sparkling welcome toast, 4 courses with a 3 oz wine pairing per course, and 18% gratuity
- Choice of 3 mains (yes, thereโs a veggie option!)
Reserve by Febuary 9th 2026.
Paglione Estate Winery
724 County Rd 50 E, Harrow
Tickets & Menu
MURDER MYSTERY DINNER – THE MIRROR MAZE
February 14th at 6:00pm
Step into an immersive evening where live theatre, mystery, and dining come together inside the surreal world of Scarehouse. The Murder Mystery Dinner is an interactive experience that places you at the center of a story filled with secrets, shifting alliances, and a crime that must be unraveled.
As the night unfolds, characters move through the space, conversations carry hidden meaning, and clues emerge organically around the room. Guests are encouraged to observe closely, interact when invited, and piece together whatโs really happening as the mystery builds toward its conclusion. This is not a show you simply watch โ itโs an experience youโre part of. The tone is playful, theatrical, and comical rather than frightening, making it perfect for couples, friend groups, and anyone looking for a unique night out that blends storytelling with great food.
Your ticket includes a full plated dinner featuring:
Fresh salad
Chicken Parmesan
Mixed vegetables
Roasted potatoes
Dessert: Affogato
Admission: From $75
Scarehouse Windsor
1441 McDougall Ave, Windsor
Event Listing
Puppy Love Night Market
February 14th from 6:00pm until 10:00pm
Looking for a fun, social way to spend Valentineโs Night? Whether youโre coming with a partner, friends, or flying solo, the Puppy Love Night Market is all about good vibes, local businesses, and a little bit of magic with the pups included!
Join us for an evening filled with local makers and pop-ups, food, drinks, and a bar, and a lineup of experiences designed to keep you mingling and hanging around. Capture the moment with an on-site photographer, explore a little mystery with psychic, palm, and tarot card readings, and enjoy a few surprise draws throughout the night.
This isnโt speed dating. Itโs not just a market.
Itโs a relaxed, dog-friendly night out where community, connection, and local love take center stage.
Come shop, sip, socialize, and see where the night takes you.
Animal Antics Behaviour Centre
3966 North Service Rd E, Windsor
Event Listing
Laughs & Love: A Valentineโs Comedy Show
February 14th from 7:00pm until 10:00pm
Celebrate Valentineโs Day with big laughs and great vibes. Featuring professional comedians and a fixed-price Valentineโs menu at the venue.
Laughs & Love: A Valentineโs Comedy Show
This Valentineโs Day, skip the clichรฉs and treat your date to something youโll actually remember โ a night of live stand-up comedy featuring professional touring comedians.
Whether youโre celebrating love, laughing through heartbreak, or just here for a great night out, this show delivers big laughs, great vibes, and an intimate live comedy experience. Each show features a rotating lineup of pro comedians, so no two shows are the same.
What to expect:
-A curated lineup of professional stand-up comedians
-A lively, high-energy comedy show perfect for couples or groups
-Fixed-price Valentineโs menus available at the venue (food & drinks sold separately unless noted)
-A fun, upscale atmosphere ideal for date night
Cherry Rock Lounge
63 Pitt St E, Windsor
Event Listing
Valentine’s day at urban field house
February 14th at 7:00pm
This Valentineโs Day, treat your special someone to an unforgettable evening filled with elegance, flavor, and romance.
Live music will enhance the ambiance with soft, melodic tunes that inspire you to savor each bite and each otherโs company.
Menu:
- Charcuterie Board for 2
- Homemade focaccia bread with whipped roasted red pepper butter
- Pear and pomegrante salad with walnuts, and crumbled feta, served with lenon ginger dressing.
- Filet mignon paired with buttery New brunswick lobster tail and succulent shrimp served with garlic mashed potatotes and aspargus.
- Flourless chocolate torte finished with raspberry coulis and chantilly cream.
Urban Field House
1203 Faith Dr, Emeryville
Event Listing
Valentine’s day at Viewpointe Estate Winery
February 14th at 7:00pm
Choose one shared appetizer, two individual mains, and one shared dessert. Wine pairings for each course optional (in addition).
Choose from:
Appetizer:
- Blackened cajun beef medallions with blue cheese cream sauce
- Lemon Dijon crab cakes with roasted red pepper aioli
- Baked brie with onion jam served with bacon bread twists
Main – served with butter and herb roasted fingerling potatoes and garlic asparagus
- Pork tenderloin Wellington with pork au jus
- Bacon fat confit duck breast with sour cherry and thyme sauce
- Cornmeal crusted Lake Erie pickerel with Veracruz sauce
- Goat cheese, roasted vegetable, and puff pastry
Dessert:
- Chocolate ganache cake with raspberry sauce
- Cappuccino creme brulee with biscoff cookie
- Spiced brown sugar bread pudding with white chocolate sauce
$150 per couple (includes HST)
Viewpointe Estate Winery
151 County Rd 50 E, Harrow
Event Listing
Valentine’s jazz night
February 14th from 8:00pm until 10:30pm
Love is in the air โ and so is the jazz.
Join us for an intimate performance by The Coffee House Combo Trio. Enjoy a night of jazz, dancing and all the cozy, candle-lit vibes.
Doors at 8PM | Show at 8:30PM
$10 per Ticket | General Admission Seating
19+ event
Please note: Seating is general admission; on a first come, first served basis. Ticket purchase guarantees a seat.
Walkerville Brewery
525 Argyle Rd, Windsor
Event Listing
