Wine + Coasters!
Join us for a fun, hands-on Sunday afternoon where creativity meets craft beverages! As part of Kalamazoo Craft Beverage Week, Sit and Stay Winery is teaming up with Freeland Fam Cookies to bring you a relaxed and creative workshop experience.
Create beautiful handmade coasters while sipping your favorite wine. No experience needed—this workshop is beginner-friendly and all about enjoying the process, good company, and great local flavor.
Sunday, February 1st
2:00–4:00 PM
Sit and Stay Winery | Kalamazoo, MI
Event highlights:
• Guided coaster-making workshop
• Wine available for purchase
• Official Kalamazoo Craft Beverage Week event
Perfect for a cozy Sunday reset—sip, create, and support local!
Guess the Wine Flight!
Guess the Wine Flight – Craft Beverage Week Special!
Join us at Sit and Stay Winery as we proudly participate in Kalamazoo Craft Beverage Week with a fun, interactive tasting experience: Guess the Wine Flight.
Put your palate to the test as you sample a curated wine flight and try to identify each pour. The better your guesses, the bigger your reward—receive $1 off for every correct guess. Whether you’re a seasoned wine enthusiast or just enjoy a good challenge, this is a relaxed and engaging way to celebrate Craft Beverage Week.
Stop in anytime during the event window and enjoy a unique tasting experience that highlights local craft beverages and community. Scan the Craft Beverage Week QR code to explore all the week has to offer!
Event Details:
February 3rd
2:00–7:30 PM
Sit and Stay Winery – 260 E Michigan Ave, Kalamazoo
Part of Kalamazoo Craft Beverage Week
No reservations required—just come ready to sip, guess, and enjoy.
Trivia + $5 drinks!
Trivia Tuesday at Sit and Stay Winery Every Tuesday in February
Think you’ve got what it takes? Grab your friends and join us for Trivia Tuesday — a weekly night of laughs, friendly competition, and great drinks!
Every Tuesday in February
6-8pm
Sit and Stay Winery: 260 E Michigan Ave., Kalamazoo, MI
$5 drink specials all night
A mix of fun, approachable trivia topics
Wine, cider, and good vibes
Come solo or bring a team — prizes, bragging rights, and a great time guaranteed. Make Tuesdays your new favorite night out!
Sushi + Wine Pairing!
Sushi + Wine at Sit and Stay Winery – Craft Beverage Week Special!
We’re excited to partner with Just Fresh to bring you a unique and delicious Sushi + Wine experience as part of Kalamazoo Craft Beverage Week!
Join us at Sit and Stay Winery for an evening where handcrafted wines meet freshly prepared sushi. Thoughtfully paired to complement each other, this event is a perfect opportunity to explore unexpected flavor combinations while celebrating the creativity of our local craft beverage community.
Whether you’re a wine lover, a sushi fan, or simply looking for a fun night out, this relaxed and flavorful experience is a must during Craft Beverage Week. Enjoy great wine, fresh food, and great company—all in one place.
Event Details:
Wednesday, February 4
6:00–8:00 PM
Sit and Stay Winery – 260 E Michigan Ave, Kalamazoo
Partnering with Just Fresh
Proud participant in Kalamazoo Craft Beverage Week
No tickets required—stop in, sip, and savor the pairing
Best Trained Human!
BEST TRAINED HUMAN COMPETITION
Sit and Stay Winery, as a special Craft Beverage Week Event, proudly presents…Step aside, good dogs—it’s time for the humans to show what they’ve got.
Do you have a well-trained human at home? One who can sit on command? Stay under pressure? Catch a hotdog mid-air like a true champion?
Bring them out to Sit and Stay Winery for our Best Trained Human Competition, where obedience, agility, and pure silliness take center stage.
Just like a classic dog show (but with fewer leashes and more wine), humans will compete in a series of playful challenges designed to test their focus, coordination, and ability to follow very important instructions. Expect laughs, friendly competition, and plenty of cheering from the sidelines.
Events may include:
• Sit & Stay (can they hold it?)
• Hotdog Catch (style points encouraged)
• Jump Distance (zoomies optional)
Sip wine, enjoy the show, and crown the ultimate Best Trained Human of the night.
February 5th
6–8 PM
Sit and Stay Winery
Come. Stay. Show us what your human can do.
Pizza + Wine Pairing!
Part of Kalamazoo Craft Beverage Week!
Wine and pizza—name a better duo. We’ll wait.
Join us at Sit and Stay Winery for a Wine & Pizza Pairing Night, featuring delicious pizza from Benny DiCarta’s and perfectly paired wines to match. This special evening is part of Kalamazoo Craft Beverage Week, so you know it’s going to be a good one!
For just $20, you’ll enjoy curated wine pairings alongside slices of crowd-favorite pizza—because great wine deserves great pizza (and vice versa).
Friday, February 6th
5:30–8:30 PM
Sit and Stay Winery | Kalamazoo, MI
$20 per person
Featuring pizza from Benny DiCarta’s
Wine pairings by Sit and Stay Winery
Kalamazoo Craft Beverage Week 2026
Grab your friends, make it dinner plans, and come celebrate local flavors, local partnerships, and one very delicious Friday night out.
Live Music with Lukas Peterson
Kick off your weekend with an evening of live music, great wine, and relaxed vibes at Sit and Stay Winery! Join us on Friday, February 6th as Lukas Peterson brings his acoustic sound to the tasting room for a night that’s perfect for date night, friend night, a well-earned night out and those out celebrating Kalamazoo Craft beverage Week! .
Settle in with a glass (or a flight!), enjoy the music, and soak up the cozy atmosphere—this is one of those nights where you’ll want to stay awhile.
Friday, February 6th
6:00–9:00 PM
Sit and Stay Winery | Kalamazoo, MI
No cover
Wine available by the glass, bottle & flight
Live acoustic music all evening
Legacy Rolls + Wine Pairing!
Legacy Rolls + Wine Pairing at Sit and Stay Winery
Part of Kalamazoo Craft Beverage Week!
Join us at Sit and Stay Winery for a delicious pairing event featuring handcrafted rolls from Legacy Table, perfectly paired with our wines for a full day of flavor and fun. This special event is part of Kalamazoo Craft Beverage Week, celebrating the best of local food and drink in Kalamazoo!
This event is sponsored by Michigan Beef Industry.
Guests can enjoy a variety of Legacy Table’s signature rolls paired with select Sit and Stay wines, making this a perfect stop whether you’re spending the day exploring KCBW events or looking for a cozy place to settle in.
Roll flavors include:
• Philly Cheesesteak
• Teriyaki
• Corn Beef
Friday, February 7th
1:00–7:00 PM
Sit and Stay Winery | Kalamazoo, MI
Wine available by the glass and flight
Proudly partnering with Legacy Table
Kalamazoo Craft Beverage Week 2026
Board Game Afternoon!
Board Game Afternoon at Sit and Stay Winery
Play. Drink. Stay.
Join us for a laid-back Sunday filled with board games, great wine, and even better company! Whether you’re a seasoned strategist or just here for the laughs, this is the perfect way to spend a cozy afternoon.
Sunday, February 8
1:00–4:00 PM
Sit and Stay Winery
260 E Michigan Ave., Kalamazoo, MI
We’ll have a variety of board games available, or feel free to bring your favorite to share. Grab a glass of wine, settle in with friends (or make new ones!), and enjoy a relaxed, playful atmosphere.
Wine and food available for purchase
Games, laughter, and community
We can’t wait to see you!
Trivia + $5 drinks!
Trivia Tuesday at Sit and Stay Winery Every Tuesday in February
Think you’ve got what it takes? Grab your friends and join us for Trivia Tuesday — a weekly night of laughs, friendly competition, and great drinks!
Every Tuesday in February
6-8pm
Sit and Stay Winery: 260 E Michigan Ave., Kalamazoo, MI
$5 drink specials all night
A mix of fun, approachable trivia topics
Wine, cider, and good vibes
Come solo or bring a team — prizes, bragging rights, and a great time guaranteed. Make Tuesdays your new favorite night out!
Craft Club!
Art. Wine. Friends.
Looking for the perfect girls’ night, a cozy midweek hang, or a reason to finally try that craft you’ve been saving on Pinterest? Welcome to Craft Club at Sit and Stay Winery!
We’re teaming up with Freelandfam Cookies to bring you a relaxed, creative night where the projects change, the wine flows, and the pressure to “be good at art” is absolutely zero. Crafts will vary each month, so there’s always something new to try—paint one night, create something totally different the next!
2nd & 4th Wednesday of every month
6:00–8:00 PM
Sit and Stay Winery | Kalamazoo, MI
What to expect:
• Guided (but low-pressure!) crafts with Freelandfam Cookies
• A fun, welcoming space—perfect for beginners
• Wine available by the glass or flight
• A great excuse for girls’ night, solo time, or meeting new friends
Bring your bestie, come solo, or make it your new midweek tradition. Sit. Stay. Create something fun.
Live music with Drew Alkema
Drew Alkema – Valentine’s Day Live Music
Saturday, February 14th
6:00–8:00 PM
Sit and Stay Winery | Kalamazoo, MI
Celebrate Valentine’s Day with the perfect blend of live music, wine, and chocolate! Join us for an intimate evening featuring Drew Alkema performing live while you sip, relax, and enjoy our special Chocolate & Wine Pairing—available just for this night.
Whether you’re coming with your sweetheart, your best friend, or treating yourself, this is the ultimate Valentine’s vibe.
What to Expect:
Live music by Drew Alkema
Handcrafted wines
Special Valentine’s chocolate & wine pairing
Cozy, romantic atmosphere
Make it a date night, girls’ night, or solo self-love night—we’ve got you covered
Community Book Swap!
Community Book Swap at Sit and Stay Winery
Wine • Books • Good Times
Sunday, February 15th
1:00–4:00 PM
Sit and Stay Winery | Kalamazoo, MI
Calling all book lovers, wine sippers, and cozy vibes seekers!
Join us for a relaxing afternoon of community, connection, and great reads at our Book Swap event. Bring 3 well-loved books you’re ready to pass along, and leave with 3 new-to-you favorites to enjoy.
Settle in with a glass of wine, browse through stories, meet fellow readers, and enjoy the kind of slow, comfy afternoon we all need.
How It Works:
Bring 3 gently loved books
Swap them for 3 new reads
Enjoy handcrafted wine
Connect with fellow book lovers
Whether you come with friends or solo, you’ll leave with new books, new connections, and a full heart (and glass).
Trivia + $5 drinks!
Trivia Tuesday at Sit and Stay Winery Every Tuesday in February
Think you’ve got what it takes? Grab your friends and join us for Trivia Tuesday — a weekly night of laughs, friendly competition, and great drinks!
Every Tuesday in February
6-8pm
Sit and Stay Winery: 260 E Michigan Ave., Kalamazoo, MI
$5 drink specials all night
A mix of fun, approachable trivia topics
Wine, cider, and good vibes
Come solo or bring a team — prizes, bragging rights, and a great time guaranteed. Make Tuesdays your new favorite night out!
Who Done it?!
Who Done It? Wednesdays at Sit & Stay Winery
Join us for an interactive, mystery night where you are the detective trying to solve a cold case.
Step into the scene, sip your favorite wine, and work with (or against!) your friends to solve the case. Whether you're a seasoned detective or just in it for fun, this evening is full of laughter, light-hearted suspense, and great wine.
The winning team will win a gift certificate.
Dates: Wednesday, Feb 18th
Time: 6:00-8:00PM
Cost: $5 per person
Location: Sit & Stay Winery, Kalamazoo, MI
Bring your curiosity, your friends, and your best detective instincts. The question is… Who Done It?
Friend Finder!
Friend Finder at Sit and Stay Winery
February 19 | 6–8 PM
New to the area? Or just feeling like you haven’t quite found your people yet? You’re not alone—and this night is for you
Friend Finder is a laid-back, welcoming evening designed to help adults connect, mingle, and build real community in a low-pressure way. No awkward icebreakers—just good wine, easy conversation, and space to be yourself.
What to expect:
Wine available for purchase
Board games out and ready
Music playing to set a relaxed, social vibe
Kalamazoo info table with local spots to explore (restaurants, places to visit, and more)
A friendly, inclusive atmosphere where it’s okay to come solo
Whether you’ve just moved to Kalamazoo, are rebuilding your social circle, or simply want to meet new faces—this night is about connection, community, and feeling like you belong.
Come as you are. Leave with new connections.
We can’t wait to welcome you
Live Music with Megan Dooley!
Live Music at Sit and Stay Winery: Megan Dooley
Friday, February 20 | 6–8 PM
Join us for a relaxed evening of great wine and live music featuring Megan Dooley!
Megan brings an engaging, feel-good sound that pairs perfectly with a glass of wine and a cozy night out.
Whether you’re winding down after the week, meeting up with friends, or looking for something fun to do on a Friday night, this is the perfect way to settle in and stay awhile.
What to expect:
Wine available for purchase
Live music from Megan Dooley
Comfortable, welcoming atmosphere
Come solo or bring friends
No tickets needed—just show up, grab a glass, and enjoy the music.
We can’t wait to see you there
Mac and Cheese Bar + Wine!
Mac & Cheese Bar + Wine Night at Sit and Stay Winery
Saturday, February 21st
5:00–7:00 PM
Sit and Stay Winery | Kalamazoo, MI
Featuring Legacy Table
Get ready for the ultimate comfort food night!
Join us for a cozy evening of creamy mac & cheese and perfectly paired wines at Sit and Stay Winery. We’re teaming up with Legacy Table to bring you a delicious Mac & Cheese Bar that’s sure to satisfy every craving.
What’s Included:
Build-your-own mac & cheese bar
Handcrafted wines
Local partnership with Legacy Table
Cozy, relaxed atmosphere
Perfect for date night, friends night, or just treating yourself to some serious comfort food
Trivia + $5 drinks!
Trivia Tuesday at Sit and Stay Winery Every Tuesday in February
Think you’ve got what it takes? Grab your friends and join us for Trivia Tuesday — a weekly night of laughs, friendly competition, and great drinks!
Every Tuesday in February
6-8pm
Sit and Stay Winery: 260 E Michigan Ave., Kalamazoo, MI
$5 drink specials all night
A mix of fun, approachable trivia topics
Wine, cider, and good vibes
Come solo or bring a team — prizes, bragging rights, and a great time guaranteed. Make Tuesdays your new favorite night out!
Craft Club!
Art. Wine. Friends.
Looking for the perfect girls’ night, a cozy midweek hang, or a reason to finally try that craft you’ve been saving on Pinterest? Welcome to Craft Club at Sit and Stay Winery!
We’re teaming up with Freelandfam Cookies to bring you a relaxed, creative night where the projects change, the wine flows, and the pressure to “be good at art” is absolutely zero. Crafts will vary each month, so there’s always something new to try—paint one night, create something totally different the next!
2nd & 4th Wednesday of every month
6:00–8:00 PM
Sit and Stay Winery | Kalamazoo, MI
What to expect:
• Guided (but low-pressure!) crafts with Freelandfam Cookies
• A fun, welcoming space—perfect for beginners
• Wine available by the glass or flight
• A great excuse for girls’ night, solo time, or meeting new friends
Bring your bestie, come solo, or make it your new midweek tradition. Sit. Stay. Create something fun.
Comedy Night!
Comedy Night at Sit and Stay Winery
Sip. Laugh. Stay.
Thursday, February 26th
6:30–8:30 PM
Sit and Stay Winery | Kalamazoo, MI
Hosted by Chris Rentrof | No Quarter Comedy
Get ready for a night full of laughs, great wine, and good vibes!
Join us at Sit and Stay Winery for Comedy Night, featuring a lineup of hilarious comedians from No Quarter Comedy, hosted by the always-funny Chris Rentrof.
Grab your favorite glass of wine (yes, even the fun flavors ), settle in, and enjoy an evening of stand-up in our cozy, welcoming space.
Perfect for date night, friends night, or a much-needed midweek laugh.
What to Expect:
Live stand-up comedy
Handcrafted wines
Big laughs in a relaxed setting
Local comedy collaboration
Come sip, laugh, and stay awhile—we can’t wait to see you there!
Live Music with Kyle Hurd
Kyle Hurd – Live Music at Sit and Stay Winery
Friday, February 27th
6:00–8:00 PM
Sit and Stay Winery | Kalamazoo, MI
Kick off your weekend with great music, great wine, and great company!
Join us at Sit and Stay Winery for an evening of live music with Kyle Hurd. His soulful sound and laid-back style pair perfectly with a cozy atmosphere and your favorite glass of wine.
Whether you’re coming for date night, a friends’ night out, or just some relaxing “me time,” this is the perfect way to unwind and enjoy local talent.
What to Expect:
Live music by Kyle Hurd
Handcrafted wines (including our fun favorites!)
Warm, welcoming vibes
Supporting local artists
Come sip, relax, and enjoy the soundtrack to your Friday night
Beach Party!
Beach Party at Sit and Stay Winery
Saturday, February 28th
6:00–8:00 PM
Sit and Stay Winery | Kalamazoo, MI
Who says you can’t have summer in February?
Join us as we chase away the winter blues and turn Sit and Stay Winery into a beachy escape for the night! We’re bringing the sunshine vibes with:
Frozen wine slushies
Live music by Neil Jansen
Your favorite wines
Laid-back summer energy
Grab your friends, throw on your best tropical vibes, and come pretend it’s summer with us—no sunscreen required!
Whether you’re dreaming of warmer days or just need a fun Saturday night out, this is your mini-vacation right here in Kalamazoo
Paint Your Pet!
🎨 Paint Your Pet at Sit & Stay Winery 🐶🐱🍷
Grab a glass of wine and turn your favorite fur baby into a work of art! Join us for a fun, relaxed afternoon where you’ll learn how to paint your pet—no experience required.
This guided class includes step-by-step instruction, all supplies, and a flight of wine to sip while you paint. Just bring a photo of your pet and get ready to create something uniquely yours!
✨ What’s included:
• All painting supplies
• Step-by-step guidance from the instructor
• A flight of wine to enjoy during class
🗓 Date: January 25th
⏰ Time: 2:00–4:00 PM
📍 Location: Sit & Stay Winery
💲 Cost: $40 per person
This is a laid-back, welcoming event—perfect for a fun afternoon out with friends, a creative date, or a little solo time doing something just for you.
Spots are limited, so be sure to save your seat. We can’t wait to see your pets come to life on canvas! 🐾🎨🍷
January Book Swap!
January Book Swap at Sit & Stay Winery
Curl up with a glass of wine and discover your next great read at our January Book Swap!
Join us for a relaxed, cozy evening of sipping, swapping, and socializing. Bring 3–5 gently used books you’ve loved and are ready to pass along, then browse the selection and take home a few new-to-you favorites.
How it works:
• Bring 3–5 gently used books
• Swap them for books brought by other guests
• Sip wine, snack, and enjoy great company
Date: January 22nd
Time: 5:30–7:30 PM
Location: Sit & Stay Winery
This is a casual, come-as-you-are event—bring your cozy favorites, grab a glass, and settle in for a fun, laid-back night with fellow book lovers
Who Done it Wednesday!
Who Done It? Wednesdays at Sit & Stay Winery
Join us for an interactive, mystery night where you are the detective trying to solve a cold case.
Step into the scene, sip your favorite wine, and work with (or against!) your friends to solve the case. Whether you're a seasoned detective or just in it for fun, this evening is full of laughter, light-hearted suspense, and great wine.
The winning team will win a gift certificate.
Dates: Wednesday, December 3rd & 17th | January 7th & 21st
Time: 5:30–7:30 PM
Cost: $5 per person
Location: Sit & Stay Winery, Kalamazoo, MI
Bring your curiosity, your friends, and your best detective instincts. The question is… Who Done It?
Wine + Soup Pairing!
Event: Soup & Wine Pairing
Date: Monday, January 15th
Time: 5:30–7:30 PM
Location: Sit and Stay Winery
Warm up your winter evening with a cozy and delicious Soup & Wine Pairing at Sit and Stay Winery!
Join us as we serve up a carefully curated selection of comforting soups perfectly paired with our handcrafted wines. Whether you’re looking for a relaxing night out, a fun date night, or just a reason to indulge in great food and wine, this event has you covered.
Details:
Expertly paired soups and wines
Cozy, welcoming atmosphere
Perfect for wine lovers and foodies alike
White Elephant Gift Exchange!
Got a gift you didn’t love? Didn’t quite fit your vibe? Or maybe it made you say “oh… wow”?
Perfect — bring it to our White Elephant Gift Exchange!
Join us at Sit and Stay Winery for a fun, laid-back afternoon of laughs, surprises, and great wine. This classic White Elephant-style exchange is all about having fun, stealing gifts, and enjoying time together — no pressure, just good energy and good pours.
Whether your gift is funny, quirky, or unexpectedly awesome, this is the place to pass it along and maybe leave with something even better.
Saturday, January 10th
3–5 PM
Sit and Stay Winery
260 E Michigan Ave., Kalamazoo
How it works:
• Bring a wrapped White Elephant-style gift
• Sip wine while gifts are opened and stolen
• Laugh a lot
Bring your friends, bring that mystery gift, and let’s keep the fun going at the winery!
Who Done it Wednesday!
Who Done It? Wednesdays at Sit & Stay Winery
Join us for an interactive, mystery night where you are the detective trying to solve a cold case.
Step into the scene, sip your favorite wine, and work with (or against!) your friends to solve the case. Whether you're a seasoned detective or just in it for fun, this evening is full of laughter, light-hearted suspense, and great wine.
The winning team will win a gift certificate.
Dates: Wednesday, December 3rd & 17th | January 7th & 21st
Time: 5:30–7:30 PM
Cost: $5 per person
Location: Sit & Stay Winery, Kalamazoo, MI
Bring your curiosity, your friends, and your best detective instincts. The question is… Who Done It?
Closed all day for a private event
Closed all day for a private event! See you on Tuesday!
Wine & Ice Cream Pairing
Here's the Scoop!
Wine + Ice Cream Pairing
Thursday, July 10 | 5–7 PM
Sit and Stay Winery | $20 per person
We’re teaming up with The Spirit of Kalamazoo to bring you the coolest tasting of the summer! For just $20, enjoy three unique wine pours, each perfectly paired with a scoop of delicious ice cream.
It’s the ultimate combo of sweet and sippable—so grab your friends and treat yourself to this one-of-a-kind flavor experience!
3 wines + 3 scoops = pure summer magic
