Events
Scott McGill & Heather Live 🎶
Friday October 16th 2026
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 2026
11:00 AM – 11:00 PM
Grace and Whiskey Live at Tailwind Tavern 🎸
Saturday October 17th 2026
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 October 20th 2026
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 2026
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 2026
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 2026
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 2026
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 2026
11:00 AM – 11:00 PM
National Sandwich Day
Tuesday November 3rd 2026
11:00 AM – 09:00 PM
New Year's Eve
Thursday December 31st 2026
11:00 AM – 11:00 PM