Music with Tequila Jim 🎵
Thursday October 15th
Join us at Tailwind Tavern for live music with Tequila Jim on October 15th, 2026! 🎸
Come settle in for an evening of live entertainment, great food, refreshing drinks, and good company right here in Hopedale. Whether you're joining us for dinner or meeting friends for a night out, Tequila Jim will provide the soundtrack for a great night at Tailwind Tavern.
Grab your crew, order your favorites, and stay for the music! 🍻
06:00 PM - 09:00 PM
Scott McGill & Heather Live 🎶
Friday October 16th
Join us at Tailwind Tavern for live music with Scott McGill & Heather! 🎵
Enjoy an evening of live entertainment while you dig into your Tailwind favorites, grab a drink, and catch up with friends.
Make us your Friday night landing spot! ✈️🍻
07:00 PM - 10:00 PM
National Pasta Day
Saturday October 17th
Because life is better with pasta!
11:00 AM - 11:00 PM
Grace and Whiskey Live at Tailwind Tavern 🎸
Saturday October 17th
Saturday night calls for live music! 🎶
Join us at Tailwind Tavern as Grace and Whiskey bring the entertainment for a night of food, drinks, music, and good company.
Bring your friends, grab a table, and spend your Saturday night with us in Hopedale. 🍻
07:00 PM - 10:00 PM
Trivia Night at Tailwind Tavern, Every Tuesday
Starting on Tuesday August 25th 2026
Every Tuesday
Test your knowledge at Wise Guys Trivia, every Tuesday night from 7 to 9pm at Tailwind Tavern in Hopedale. Gather your team, grab a cold drink and a plate of our bar and grill favorites, and play for bragging rights. Whether you are a trivia regular or trying it for the first time, it is one of the best weeknight things to do in Hopedale. No cover, no reservation needed, just show up ready to compete.
Tailwind Tavern, 1 Menfi Way, Hopedale, MA. Call 508-381-0847 or visit tailwindtavernma.com.
07:00 PM - 09:00 PM
Jaen Mannion Live at Tailwind Tavern 🎵
Thursday October 22nd
Join us from 6–9 PM for live music with Jaen Mannion at Tailwind Tavern! 🎶
It’s the perfect excuse to get out of the house, enjoy dinner and drinks, and spend the evening listening to live music.
Grab your favorite people and meet us at Tailwind! 🍻
06:00 PM - 09:00 PM
Matt Tremble Live at Tailwind Tavern 🎸
Friday October 23rd
Start your weekend at Tailwind Tavern with live music from Matt Tremble! 🎵
Come hungry, grab your favorite drink, and enjoy an evening of live entertainment and good company in Hopedale.
Dinner + drinks + live music sounds like a pretty good Friday night to us. 🍻
07:00 PM - 10:00 PM
Matt Broduer Live at Tailwind Tavern 🎶
Saturday October 24th
Spend your Saturday night with Matt Broduer live at Tailwind Tavern! 🎸
Bring your friends and settle in for an evening of live entertainment, great food, refreshing drinks, and that welcoming Tailwind atmosphere.
Come for dinner. Stay for the music. 🍻
07:00 PM - 10:00 PM
Charlie Rocks Live at Tailwind Tavern 🎃🎸
Friday October 30th
Get your Halloween weekend started with Charlie Rocks live at Tailwind Tavern! 🎶
Join us on October 30 for live music, great food, drinks, and a fun night out just before Halloween.
Grab your crew and kick off the spooky weekend at your neighborhood tavern! 🎃🍻
07:00 PM - 10:00 PM
Halloween
Saturday October 31st
Bring your best costume and join us on Halloween!
11:00 AM - 11:00 PM
National Sandwich Day
Tuesday November 3rd
Because food tastes better between bread!
11:00 AM - 09:00 PM
New Year's Eve
Thursday December 31st
Celebrate the New Year with us and join us on New Year's Eve!
11:00 AM - 11:00 PM