Member Winery Events
October 2025
Sparkling Hours
Thu. Oct 02 to Fri. Oct 03
South Shore Wine Company
All sparkling wines by the glass $1 off.
Sparkling Hours
Thu. Oct 02 to Fri. Oct 03
South Shore Wine Company
All sparkling wines by the glass $1 off.
Draft Nights
Thu. Oct 02 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
$2 off draft beers, with a good chance of informal live music.
Mazzmosa Weekends
Sat. Oct 04 to Sun. Oct 05
South Shore Wine Company
Mimosas and mimosa flights available.
Slushie Sundays
Sun. Oct 05 @ 3:00 pm - 4:00 pm
South Shore Wine Company
Slushies available at special price of $6 all day.
Sparkling Hours
Thu. Oct 09 to Fri. Oct 10
South Shore Wine Company
All sparkling wines by the glass $1 off.
Sparkling Hours
Thu. Oct 09 to Fri. Oct 10
South Shore Wine Company
All sparkling wines by the glass $1 off.
Draft Nights
Thu. Oct 09 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
$2 off draft beers, with a good chance of informal live music.
Cousins Maine Lobster and Costume Contest
Fri. Oct 10 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
Cousins Maine Lobster Food Truck with live music from Daniel Cecil.
Mazzmosa Cidermosa Weekends
Sat. Oct 11 to Sun. Oct 12
Mazza Vineyards
Check out new Cidermosa seasonal flights
Mazzmosa Weekends
Sat. Oct 11 to Sun. Oct 12
South Shore Wine Company
Mimosas and mimosa flights available.
Cellar Jams with Acoustic Cup of Joe
Sat. Oct 11 @ 6:00 pm - 9:00 pm
Cellar '54
Live music with Acoustic Cup of Joe
Mazzmosa Cidermosa Weekends
Sun. Oct 12 to Mon. Oct 13
Mazza Vineyards
Check out new Cidermosa seasonal flights
CWC Brushed Info Event & Live Music
Sun. Oct 12 @ 1:00 pm - 4:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
Details TBA--checkout our Facebook page @fivend20
Slushie Sundays
Sun. Oct 12 @ 3:00 pm - 4:00 pm
South Shore Wine Company
Slushies available at special price of $6 all day.
Sundays at the Cellar
Sun. Oct 12 @ 4:00 pm - 6:00 pm
6 Mile Cellars
Live jazz with the Bob Smith Quartet.
Sparkling Hours
Thu. Oct 16 to Fri. Oct 17
South Shore Wine Company
All sparkling wines by the glass $1 off.
Sparkling Hours
Thu. Oct 16 to Fri. Oct 17
South Shore Wine Company
All sparkling wines by the glass $1 off.
Draft Nights
Thu. Oct 16 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
$2 off draft beers, with a good chance of informal live music.
Customer Appreciation Night
Fri. Oct 17 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
Live music with Tom Robert.
Mazzmosa Cidermosa Weekends
Sat. Oct 18 to Sun. Oct 19
Mazza Vineyards
Check out new Cidermosa seasonal flights
Mazzmosa Weekends
Sat. Oct 18 to Sun. Oct 19
South Shore Wine Company
Mimosas and mimosa flights available.
Courtyard Winery Magic Show
Sat. Oct 18 @ 2:00 pm - 3:00 pm
Courtyard Winery
Magic show!
Cellar Jams with Acoustics by Denny and Heather
Sat. Oct 18 @ 6:00 pm - 8:00 pm
Cellar '54
Live music with Denny and Heather
Mazzmosa Cidermosa Weekends
Sun. Oct 19 to Mon. Oct 20
Mazza Vineyards
Check out new Cidermosa seasonal flights
Sunday Jams with Abby Elwell
Sun. Oct 19 @ 1:00 pm - 3:00 pm
Cellar '54
Live music with Abby Elwell.
Slushie Sundays
Sun. Oct 19 @ 3:00 pm - 4:00 pm
South Shore Wine Company
Slushies available at special price of $6 all day.
Sundays at the Cellar
Sun. Oct 19 @ 4:00 pm - 6:00 pm
6 Mile Cellars
Live music with Midnight Frolic
Sparkling Hours
Thu. Oct 23 to Fri. Oct 24
South Shore Wine Company
All sparkling wines by the glass $1 off.
Sparkling Hours
Thu. Oct 23 to Fri. Oct 24
South Shore Wine Company
All sparkling wines by the glass $1 off.
Draft Nights
Thu. Oct 23 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
$2 off draft beers, with a good chance of informal live music.
Customer Appreciation Night
Fri. Oct 24 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
Live music with Jeremy Jaeger.
Mazzmosa Cidermosa Weekends
Sat. Oct 25 to Sun. Oct 26
Mazza Vineyards
Check out new Cidermosa seasonal flights
Mazzmosa Weekends
Sat. Oct 25 to Sun. Oct 26
South Shore Wine Company
Mimosas and mimosa flights available.
Trick or Treat for Grown-ups
Sat. Oct 25 to Sun. Oct 26
Liberty Vineyards & Winery
Wine & Halloween Candy Pairing
Singo: Halloween
Sat. Oct 25 @ 3:00 pm - 5:00 pm
Liberty Vineyards & Winery
Singo is similar to Bingo, but with great music instead of numbers
Cellar Jams with Tito & Dave
Sat. Oct 25 @ 6:00 pm - 8:00 pm
Cellar '54
Live music with Tito & Dave.
Mazzmosa Cidermosa Weekends
Sun. Oct 26 to Mon. Oct 27
Mazza Vineyards
Check out new Cidermosa seasonal flights
Slushie Sundays
Sun. Oct 26 @ 3:00 pm - 4:00 pm
South Shore Wine Company
Slushies available at special price of $6 all day.
Sundays at the cellar
Sun. Oct 26 @ 4:00 pm - 6:00 pm
6 Mile Cellars
Live music with We. The Duo
Sparkling Hours
Thu. Oct 30 to Fri. Oct 31
South Shore Wine Company
All sparkling wines by the glass $1 off.
Sparkling Hours
Thu. Oct 30 to Fri. Oct 31
South Shore Wine Company
All sparkling wines by the glass $1 off.
Draft Nights
Thu. Oct 30 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
$2 off draft beers, with a good chance of informal live music.
Customer Appreciation Night
Fri. Oct 31 @ 5:00 pm - 8:00 pm
Mazza Chautauqua Cellars / Five & 20 Spirits & Brewing
Live music with Shani Bills.