Mother’s Day Pop-Up Shopping Event

Join us for a sweet and relaxing afternoon as we celebrate all the amazing moms in our lives!

Saturday, May 2nd | 1–4 PM

Grab your favorite people and come sip, shop, and enjoy a cozy afternoon at the winery. We’ll have a curated selection of local vendors—perfect for finding thoughtful, one-of-a-kind gifts just in time for Mother’s Day (or treating yourself… because you deserve it ).

Sip on your favorite wines
Shop unique, local finds
Celebrate the women you love

Whether you’re shopping for mom, with mom, or as the mom who needs a little outing—this is the perfect way to spend your afternoon

May Art Hop at Sit and Stay Winery

Join us for a fun and relaxing evening at the winery as we celebrate local art and great wine!
We’re excited to feature talented local artist Charlotte Billingsley during this special Art Hop event. Come explore her work, connect with the artist, and enjoy the creative atmosphere.

Event Details:
May 1st
5:00–8:00 PM
Sit and Stay Winery

Stop in, sip on our delicious handcrafted wines, and support a local artist—it’s the perfect end of week outing with friends or a cozy date night! No tickets needed—just come as you are and enjoy the evening with us.

We can’t wait to see you there!

Live Music at Sit and Stay Winery!

Join us for a laid-back Sunday afternoon filled with great music, good vibes, and your favorite wines! Tim Just Tim Music will be playing live from 2–4 PM—bringing the perfect soundtrack for sipping, relaxing, and soaking in a spring day.

Grab your friends, bring your crew, and settle in for an easygoing afternoon at the winery. Whether you're here for a glass (or a flight ), the music, or just the atmosphere—you won’t want to miss it!

Sunday, April 26th
2–4 PM
Sit and Stay Winery

Cheers to sunshine, live tunes, and wine time!

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 The Pensioners

Join us for a relaxing afternoon of great wine and live music at Sit and Stay Winery!The Pensioners are bringing their acoustic sound and feel-good tunes—perfect for sipping, unwinding, and enjoying a cozy spring day with friends

Sunday, April 19th
2–4 PM
Sit and Stay Winery

Grab a glass (or a bottle ), find your spot, and let the music set the tone for your afternoon No tickets needed—just come, sip, and stay awhile

Join us at Sit & Stay Winery for a cozy evening of bookish fun at our Book Swap! 📚🍷

🗓 April 16th
⏰ 6-8 PM
📍 Sit & Stay Winery – Kalamazoo, MI

Here’s how it works:
Bring 3 books you’re ready to part with and leave with 3 new-to-you reads! It’s the perfect way to refresh your bookshelf, discover something unexpected, and connect with fellow book lovers.

All genres are welcome — fiction, nonfiction, thrillers, romance, memoirs, you name it. Just make sure the books are in good condition and ready for a new home.

Grab a glass of wine, browse the tables, chat about your favorite reads, and enjoy a relaxed, cozy night at the winery. 🍷✨

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.

Looking for the perfect way to spend a chill Sunday? We’ve got you covered.

Join us every Sunday in March from 1–4 PM for Board Game Sundays! Bring your friends (or meet some new ones), grab a glass, and settle in for an afternoon of laughs, strategy, and just the right amount of friendly competition.
We’ll have a variety of board games available to play — but you’re absolutely welcome to bring your own favorites, too!

Board games ready to play (or BYO!)
Wine flowing
Wine + Flatbread Special for just $15!

It’s cozy. It’s relaxed. It’s the kind of Sunday that makes Monday feel a little less rude.

Looking for the perfect way to spend a chill Sunday? We’ve got you covered.

Join us every Sunday in March from 1–4 PM for Board Game Sundays! Bring your friends (or meet some new ones), grab a glass, and settle in for an afternoon of laughs, strategy, and just the right amount of friendly competition.
We’ll have a variety of board games available to play — but you’re absolutely welcome to bring your own favorites, too!

Board games ready to play (or BYO!)
Wine flowing
Wine + Flatbread Special for just $15!

It’s cozy. It’s relaxed. It’s the kind of Sunday that makes Monday feel a little less rude.

Join us at Sit & Stay Winery for a laid-back evening of Live Music with Matt Borr!

Friday, March 13th
6–8 PM
Sit & Stay Winery | Kalamazoo, MI

Kick off your weekend with great wine, cozy vibes, and live acoustic music from Matt Borr. Whether you’re meeting friends, planning a date night, or just looking for a relaxing Friday out, this is the perfect way to unwind.

Grab a glass (or a bottle ), settle in, and enjoy an evening of feel-good tunes in our welcoming winery atmosphere.
No cover — just good music, good wine, and good company.

Join us at Sit & Stay Winery for a cozy evening of bookish fun at our Book Swap! 📚🍷

🗓 March 19th
⏰ 5–7 PM
📍 Sit & Stay Winery – Kalamazoo, MI

Here’s how it works:
Bring 3 books you’re ready to part with and leave with 3 new-to-you reads! It’s the perfect way to refresh your bookshelf, discover something unexpected, and connect with fellow book lovers.

All genres are welcome — fiction, nonfiction, thrillers, romance, memoirs, you name it. Just make sure the books are in good condition and ready for a new home.

Grab a glass of wine, browse the tables, chat about your favorite reads, and enjoy a relaxed, cozy night at the winery. 🍷✨

Looking for the perfect way to spend a chill Sunday? We’ve got you covered.

Join us every Sunday in March from 1–4 PM for Board Game Sundays! Bring your friends (or meet some new ones), grab a glass, and settle in for an afternoon of laughs, strategy, and just the right amount of friendly competition.
We’ll have a variety of board games available to play — but you’re absolutely welcome to bring your own favorites, too!

Board games ready to play (or BYO!)
Wine flowing
Wine + Flatbread Special for just $15!

It’s cozy. It’s relaxed. It’s the kind of Sunday that makes Monday feel a little less rude.

Sip, Snack, and Get Lucky!
Looking for the perfect way to celebrate St. Patrick’s Day? Leave the luck to the Irish and bring your skills to our St. Paddy’s Cookie Decorating Workshop!

Join us on Saturday, March 14th for an afternoon of creative fun. Whether you're a decorating pro or just here for the wine, you’ll have a blast "greening up" your very own set of delicious cookies.

What’s Included:

The Goods: A full set of festive cookies (shamrocks, gold pots, and more!) plus all the icing and supplies you need.

The Sips: Enjoy a glass of your favorite wine while you work

The Fun: A relaxed, guided environment perfect for a girls' night out, mother-daughter date, or a solo creative escape.

The Details

When: Saturday, March 14th

Where: Sit and Stay Winery- 260 E Michigan Ave. Kalamazoo MI

Time: 2:00 PM – 4:00 PM

Spaces are limited and our workshops fill up fast! Grab your spot today and let’s get ready to sham-rock and roll.

Join us at Sit & Stay Winery for a laid-back evening of Live Music with Matt Borr!

Friday, March 13th
6–8 PM
Sit & Stay Winery | Kalamazoo, MI

Kick off your weekend with great wine, cozy vibes, and live acoustic music from Matt Borr. Whether you’re meeting friends, planning a date night, or just looking for a relaxing Friday out, this is the perfect way to unwind.

Grab a glass (or a bottle ), settle in, and enjoy an evening of feel-good tunes in our welcoming winery atmosphere.
No cover — just good music, good wine, and good company.

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.

Looking for the perfect way to spend a chill Sunday? We’ve got you covered.

Join us every Sunday in March from 1–4 PM for Board Game Sundays! Bring your friends (or meet some new ones), grab a glass, and settle in for an afternoon of laughs, strategy, and just the right amount of friendly competition.
We’ll have a variety of board games available to play — but you’re absolutely welcome to bring your own favorites, too!

Board games ready to play (or BYO!)
Wine flowing
Wine + Flatbread Special for just $15!

It’s cozy. It’s relaxed. It’s the kind of Sunday that makes Monday feel a little less rude.

Live Music with Aaron Perry 
 March 6th |  6–8 PM

Join us at Sit & Stay Winery for an evening of live music with Aaron Perry — happening during Friday's Art Hop!
Make us part of your Art Hop route and stop in for:
 Live acoustic music
 Your favorite wines
 Delicious bites
 All the creative, community vibes

Whether you’re out exploring downtown or looking for the perfect cozy spot to settle in for the night, this is your sign. Grab a glass, enjoy the music, and soak up the Friday energy.