Live Music at Sit and Stay Winery

Join us on Sunday, June 7 from 2–4 PM as we welcome the incredibly talented Megan Dooley to Sit and Stay Winery!
Enjoy an afternoon of live music, great wine, and relaxing summer vibes in the heart of downtown Kalamazoo. Megan brings an energetic and soulful performance that pairs perfectly with your favorite glass of wine, cider, or sangria.

Grab your friends, sip, stay, and sing along with us for an unforgettable afternoon of music and fun!

Sit and Stay Winery
260 E Michigan Ave., Kalamazoo, MI
Sunday, June 7 | 2–4 PM

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 AT SIT & STAY WINERY

Spend your Sunday afternoon with us as we welcome Brian McClure for a live performance you won’t want to miss!
Blending rich violin melodies with acoustic charm, Brian brings a unique and captivating sound that pairs perfectly with a glass of your favorite wine. It’s the kind of laid-back, feel-good afternoon that Sundays were made for.

Sunday, May 24th
2:00 – 4:00 PM

Grab your friends, find your favorite spot, and enjoy an afternoon of live music, great wine, and cozy winery vibes.
No cover—just come ready to sip, relax, and enjoy!
See you at the winery!

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

🗓 May 21st
⏰ 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. 🍷✨

LIVE MUSIC AT SIT & STAY WINERY

Get ready for an afternoon of incredible live music with Markus & Tiffany Shelton!

This dynamic duo brings a mix of soulful vocals, piano, and acoustic energy that creates the perfect vibe for a relaxing Sunday at the winery. Whether you're here to unwind, catch up with friends, or discover your new favorite performers—this is the place to be.
Sunday, May 17th
2:00 – 4:00 PM

Pour a glass, grab a seat, and enjoy the music in our cozy, welcoming space.
No cover—just great wine, great music, and great company.

We’ll see you there!

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 AT SIT & STAY WINERY

Join us for an afternoon of great music, great wine, and even better vibes!

We’re excited to welcome Tom Noack for his “12 String Memories” live performance—a perfect blend of nostalgic tunes and feel-good favorites that you’ll want to sip and sing along to.

Sunday, May 10th
2:00 – 4:00 PM

Grab your friends, order your favorite glass (or bottle ), and settle in for a relaxing Sunday filled with music and community. Whether you're here for the melodies, the memories, or the wine—this is one you won’t want to miss!
No cover—just come ready to unwind and enjoy.

See you at the winery

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.