Thursday, 6:30pm - 8:30pm
October 09, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
October 09, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:00pm - 8:00pm
October 09, 2025
6:00pm - 8:00pm
8986 First Street
Baroda
(directions)
Play Plant Bingo at Chill Hill Winery! Win fun plant prizes, sip wine, and enjoy a cozy fall evening.
Admission: $20
Thursday, 7:00pm - 8:00pm
October 09, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Friday, 7:00pm - 10:00pm
October 10, 2025
7:00pm - 10:00pm
https://events.humanitix.com/an-evening-with-dylan-raymond-at-the-livery-yteb2d4k
190 5th St.
Benton Harbor
(directions)
Raised in Indiana, Dylan Raymond grew up on 90s country and began playing guitar at eight years old which set the stage for his musical ambitions.
Admission: $10
Saturday, 11:30am - 1:30am
October 11, 2025
11:30am - 1:30pm
6991 Ryno Rd
Coloma
(directions)
Welcome to Paint & Sip at Filkins Vineyards! Join us for a fun and relaxing afternoon of painting and sipping at the beautiful Filkins Vineyards. No prior painting experience is needed. Wine is a la carte. Ages 13 and Up!
Admission: $30
Saturday, 7:00pm - 11:00pm
October 11, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Buffalo Galaxy is where heavy hitting psychedelia meets old timin’ bluegrass. Their songwriting, patience, and personalities prove they can go deeper than your typical bluegrass band.
Admission: $10
Sunday, 2:00pm - 4:00pm
October 12, 2025
2:00pm - 4:00pm
11945 Red Arrow Hwy
Sawyer
(directions)
Experience the smooth vocals of Sally Stine live at Solasta Winery!
Admission: Free Admission
Monday, 5:30pm - 7:30pm
October 13, 2025
5:30pm - 7:30pm
15475 Walton Rd
Buchanan
(directions)
Free live outdoor music every Monday evening from May-Oct. in the beer garden at River Saint Joe!
Admission: Free
Thursday, 6:30pm - 8:30pm
October 16, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
October 16, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 7:00pm - 8:00pm
October 16, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Friday, 11:00am - 7:00am
October 17, 2025 - October 19, 2025
11945 Red Arrow Hwy
Sawyer
(directions)
Experience the beauty of fall at Solasta Winery during our Fall Harvest Weekend!
Admission: Free admission
Saturday, 11:30am - 1:30am
October 18, 2025
11:30am - 1:30pm
6991 Ryno Rd
Coloma
(directions)
Welcome to Paint & Sip at Filkins Vineyards! Join us for a fun and relaxing afternoon of painting and sipping at the beautiful Filkins Vineyards. No prior painting experience is needed. Wine is a la carte. Ages 13 and Up!
Admission: $30
Saturday, 4:00pm - 6:00pm
October 18, 2025
4:00pm - 6:00pm
6991 Ryno Rd
Coloma
(directions)
Come Line Dance with Filkins Vineyards! This class is led by Sunset Coast Country Dancers.
Admission: Free
Saturday, 4:00pm - 6:00pm
October 18, 2025
4:00pm - 6:00pm
8986 First Street
Baroda
(directions)
Pumpkin Sangria is back—let’s party! Celebrate fall with music, drinks, and harvest vibes at Chill Hill!
Admission: Free
Saturday, 11:00am - 7:00am
October 18, 2025
11:00am - 7:00pm
10983 Hills Road
Baroda
(directions)
Celebrate the flavors of fall at Apple Fest at Round Barn Winery & Estate!
Admission: Cover Charge = $5 (21+)
Sunday, 2:00pm - 4:00pm
October 19, 2025
2:00pm - 4:00pm
11945 Red Arrow Hwy
Sawyer
(directions)
Feel the rhythm of fall with Brian McClure’s fiddle tunes— the perfect pairing of music and wine.
Admission: Free admission
Monday, 5:30pm - 7:30pm
October 20, 2025
5:30pm - 7:30pm
15475 Walton Rd
Buchanan
(directions)
Free live outdoor music every Monday evening from May-Oct. in the beer garden at River Saint Joe!
Admission: Free
Thursday, 6:30pm - 8:30pm
October 23, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
October 23, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:15pm - 7:45pm
October 23, 2025
6:15pm - 7:45pm
321 State Street
St. Joseph
(directions)
Come learn the fundamentals of reading tarot cards while enjoying an evening at Lazy Ballerina Winery!
Admission: $50
Thursday, 7:00pm - 8:00pm
October 23, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Friday, 5:00pm - 9:00pm
October 24, 2025
5:00pm - 9:00pm
https://checkout.square.site/merchant/MLH7H6N49QYZM/checkout/7EI6V6A54WJDRJJFHTTTRW6V
8986 First Street
Baroda
(directions)
Celebrate Halloween at Chill Hill-O-Ween—costumes, prizes, and spooky sips with friends in Baroda, MI!
Admission: $5 per person
Friday, 6:00pm - 8:00pm
October 24, 2025
6:00pm - 8:00pm
8986 First Street
Baroda
(directions)
Craft terrariums, bath bombs & more—then party in costume at Chill Hill’s Autumn Nights Craft & Chill!
Admission: $30
Saturday, 11:30am - 1:30am
October 25, 2025
11:30am - 1:30pm
6991 Ryno Rd
Coloma
(directions)
Welcome to Paint & Sip at Filkins Vineyards! Join us for a fun and relaxing afternoon of painting and sipping at the beautiful Filkins Vineyards. No prior painting experience is needed. Wine is a la carte. Ages 13 and Up!
Admission: $30
Sunday, 1:00pm - 3:00pm
October 26, 2025
1:00pm - 3:00pm
9151 1st St
Baroda
(directions)
Think you know your spooky stuff? Test your knowledge at Halloween Trivia Night at Round Barn Brewery & Public House!
Sunday, 2:00pm - 4:00pm
October 26, 2025
2:00pm - 4:00pm
11945 Red Arrow Hwy
Sawyer
(directions)
Join us for an afternoon of soulful music with the talented Morgan Ingle. Sip, relax, and soak in the sounds at Solasta Winery!
Admission: Free admission
Thursday, 6:30pm - 8:30pm
October 30, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
October 30, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:00pm - 8:00pm
October 30, 2025
6:00pm - 8:00pm
9151 1st St.
Baroda
(directions)
This October, bingo gets a spooky twist! Join us for Boos & Bingo, a night filled with festive fun, thrilling prizes, and plenty of seasonal spirits.
Thursday, 7:00pm - 8:00pm
October 30, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Saturday, 11:30am - 1:30am
November 01, 2025
11:30am - 1:30pm
6991 Ryno Rd
Coloma
(directions)
Welcome to Paint & Sip at Filkins Vineyards! Join us for a fun and relaxing afternoon of painting and sipping at the beautiful Filkins Vineyards. No prior painting experience is needed. Wine is a la carte. Ages 13 and Up!
Admission: $30
Saturday, 11:00am - 6:00am
November 01, 2025 - November 02, 2025
10983 Hills Road
Baroda
(directions)
Celebrate spooky season in Southwest Michigan wine country with Hallowine at Round Barn Winery & Estate!
Admission: Saturday Cover Charge: $5 for 21+
Saturday, 7:00pm - 11:00pm
November 01, 2025
7:00pm - 11:00pm
10983 Hills Road
Baroda
(directions)
This Halloween, the Round Barn transforms into the ultimate haunted dance floor! Join us for a night of spine-tingling fun, thrilling beats, and festive cocktails.
Thursday, 6:30pm - 8:30pm
November 06, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
November 06, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:30pm - 8:00pm
November 06, 2025
6:30pm - 8:00pm
https://checkout.square.site/merchant/MLH7H6N49QYZM/checkout/52UZPFKXP6K3RNGR7DFOYZSG
8986 First Street
Baroda
(directions)
Test your ‘70s knowledge at Chill Hill Trivia Night! Prizes, drinks, and groovy fun await.
Admission: $20 per person
Thursday, 6:00pm - 8:00pm
November 06, 2025
6:00pm - 8:00pm
https://checkout.square.site/merchant/MLH7H6N49QYZM/checkout/GBUWU4MRN7QI5XVRNLHWHT6H
8986 First Street
Baroda
(directions)
Get crafty with friends at Chill Hill! Join our Junk Journal workshop—supplies and welcome drink included.
Admission: $20 per person
Thursday, 7:00pm - 8:00pm
November 06, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Thursday, 6:30pm - 8:30pm
November 13, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
November 13, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 7:00pm - 8:00pm
November 13, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Friday, 6:00pm - 8:00pm
November 14, 2025
6:00pm - 8:00pm
8986 First Street
Baroda
(directions)
Grab a brush and a drink - create your own glowing night sky at Chill Hill!
Admission: $38 per person
Thursday, 6:30pm - 8:30pm
November 20, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
November 20, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 7:00pm - 8:00pm
November 20, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Friday, 4:00pm - 9:00pm
November 21, 2025 - November 22, 2025
185 Mt Tabor Rd
Buchana
(directions)
Celebrate the flavors of Michigan with our annual Wild Game Weekend Dinner at Tabor Hill Winery & Restaurant.
Sunday, 1:00pm - 3:00pm
November 23, 2025
1:00pm - 3:00pm
9151 1st St.
Baroda
(directions)
Kick off the holiday season with a night of laughs, good food, and friendly competition at Thanksgiving Trivia Night at Round Barn Brewery & Public House!
Thursday, 6:30pm - 8:30pm
November 27, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
November 27, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 7:00pm - 8:00pm
November 27, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Saturday, 12:00pm - 5:00pm
November 29, 2025
12:00pm - 5:00pm
10983 Hills Road
Baroda
(directions)
Celebrate and support local this holiday season at the Small Business Saturday Market at Round Barn Winery & Estate.
Thursday, 6:30pm - 8:30pm
December 04, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
December 04, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:30pm - 8:00pm
December 04, 2025
6:30pm - 8:00pm
https://checkout.square.site/merchant/MLH7H6N49QYZM/checkout/JVQGAOIUYKWNV475NFVI6IOV
8986 First Street
Baroda
(directions)
Test your holiday smarts and rock your ugliest sweater at Chill Hill’s Christmas Trivia Night!
Admission: $20 per person
Thursday, 7:00pm - 8:00pm
December 04, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Saturday, 11:00am - 4:00am
December 06, 2025
11:00am - 4:00pm
8986 First Street
Baroda
(directions)
Find unique gifts and sip hot hard cider—Chill Hill Christmas Market is your holiday destination!
Admission: Free
Thursday, 6:30pm - 8:30pm
December 11, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
December 11, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 6:00pm - 8:00pm
December 11, 2025
6:00pm - 8:00pm
9151 1st St.
Baroda
(directions)
Bingo with a holiday twist! Gather your friends and join us for Jingle Bingo, a merry night of games, prizes, and seasonal cheer.
Thursday, 6:00pm - 8:00pm
December 11, 2025
6:00pm - 8:00pm
8986 First Street
Baroda
(directions)
Make it a merry night! Join Chill Hill’s Grinch Gnome Painting Class and craft your holiday gnome.
Admission: $35 per person
Thursday, 7:00pm - 8:00pm
December 11, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Saturday, 12:00pm - 5:00pm
December 13, 2025
12:00pm - 5:00pm
10983 Hills Road
Baroda
(directions)
Get into the holiday spirit at our December Holiday Market, where the vineyard transforms into a festive winter marketplace.
Thursday, 6:30pm - 8:30pm
December 18, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 7:00pm - 11:00pm
December 18, 2025
7:00pm - 11:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke Night At The Livery! Every Thursday. Every voice welcomed. Every performance celebrated.
Admission: Free!
Thursday, 7:00pm - 8:00pm
December 18, 2025
7:00pm - 8:00pm
190 5th St.
Benton Harbor
(directions)
Karaoke!
Admission: Free!
Saturday, 10:00am - 1:30am
December 20, 2025
10:00am - 1:30pm
185 Mt Tabor Rd
Buchana
(directions)
Celebrate the magic of the season with our annual Santa Brunch at Tabor Hill!
Sunday, 1:00pm - 3:00pm
December 21, 2025
1:00pm - 3:00pm
9151 1st St.
Baroda
(directions)
Test your holiday knowledge and celebrate the season with a festive night of Christmas Trivia!
Thursday, 6:30pm - 8:30pm
December 25, 2025
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Wednesday, 4:00pm - 8:30pm
December 31, 2025
4:00pm - 8:30pm
185 Mt Tabor Rd
Buchanan
(directions)
Close out the year in style at Tabor Hill Winery & Restaurant. Our annual New Year’s Eve Dinner features a special holiday-inspired menu.
Thursday, 6:30pm - 8:30pm
January 01, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
January 08, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
January 15, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
January 22, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
January 29, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
February 05, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
February 12, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
February 19, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
February 26, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
March 05, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
March 12, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
March 19, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
March 26, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE
Thursday, 6:30pm - 8:30pm
April 02, 2026
6:30pm - 8:30pm
92500 CR 690
Dowagiac
(directions)
Trivia Night
Admission: FREE