Island Pickle

Island Pickle Ribbon Cutting
2026-01-23 07:00 - 12:00 (America/New_York)
Join us for a full morning of events as we celebrate the Ribbon Cutting at Island Pickle! We will feature FREE Open Play (Public Welcome) from 9:00-noon. Tours of the facility and light refreshments will be served. More details to follow.

Ribbon Cutting Classic / New Beginnings 2026 Pickleball Tournament
2026-01-24 07:00 - 2026-01-25 21:00
Join us for a round robin pickleball tournament. Open to the public this tournament will feature a Round Robin format with Advanced and Intermedate Levels for Men, Women and Mixed. Open to 10 teams per group with a minimum of 10 matches per team. Medals and plenty of door prizes will be available to win!

Register here: https://pickleballtournaments.com/tournaments/10844b53-8227-4929-a8c3-a937facf44d1

Cornhole Tuesdays with Mixed Nuts
2026-01-27 18:00 - 21:00, 2026-02-03 18:00 - 21:00, 2026-02-10 18:00 - 21:00, 2026-02-17 18:00 - 21:00, 2026-02-24 18:00 - 21:00, 2026-03-03 18:00 - 21:00, 2026-03-10 18:00 - 21:00, 2026-03-17 18:00 - 21:00 and 3 more dates
Join us for Cornhole every Tuesday – hosted by Mixed Nuts! Open to the public – the first 28 people (2 man teams) who sign up will play.
$15 per player
Download the Scoreholio app and sign up your team today!

Super Bowl Watch Party
2026-02-08 17:00 - 22:00
Golf Simulator SUPER BOWL LX Watch Party

Watch the biggest game of the year in your own private golf simulator bay for up to 8 people.
Simulator Watch Party Package – $250

Includes:

Private Simulator Rental from 5PM–End of Game
2 Dozen Wings
Chip Trio
2 Pitchers of Beer (Kona, Mich Ultra, Sam Cold Snap)
Pineapple Hoisin Pork Belly Bites
Soft Pretzel & Beer Cheese

Live Entertainment | 3–6PM • Food Specials All Day

Limited simulators available — reserve yours by calling the front desk (774)228-7611

Callaway Performance Fitting Event
2026-02-14 11:00 - 15:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
We are excited to hold a Callaway Performance Fitting Event at Island Pickle on February 14th, from 11:00am – 3:00pm.
Get Ready To Make The Leap With Quantum
Work one-on-one with Callaway’s expert fitters to dial in the newest Callaway Quantum Driver with Tri-Force Face, precision-built to maximize your distance, speed, and consistency. Sign up for your fitting today!
A Quantum driver fitting with an expert fitter and the latest technology are designed to help you not only achieve more distance, but also more consistency.
Sign up today!

Wine & Nine Golf
2026-02-14 18:00 - 21:00
Bring your favorite golf partner for our first ever Wine & Nine golf event. Compete in a 9 hole golf tournament on our Trackman simulators while you enjoy complimentary charcuterie board, and then relax and enjoy an Valentine’s-inspired, 3-course dinner and wine tasting. $200 per couple. Sign up using the Island Pickle app.

Bingo (for everyone) with the Big Dill
2026-02-18 15:00 - 17:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Get ready for a lively afternoon of laughs, prizes, and friendly competition at Island Pickle! Join us for Bingo hosted by the one and only Big Dill (a/k/a Bill), bringing his signature energy and humor to every round. Open to all ages – don’t miss it!

Live Music with Monomoy Sound
2026-02-20 19:00 - 21:00
Enjoy the jazzy coastal textures and beach party vibes with Monomoy Sound – a Cape-based band writing and performing original songs with Cape Cod inspired themes. Performing live in the Tavern this event is free to patrons!

Single AF - A Post Valentine's Day Social
2026-02-28 17:30 - 20:30
Valentine’s Day is over — now it’s time to actually have fun.
BUY YOUR $10 TICKET HERE: https://www.zeffy.com/en-US/ticketing/single-af
Join us Saturday, February 28, 2026, from 5:30–8:30 PM at Island Pickle (51 Evergreen Circle, Mashpee, MA) for a relaxed, inclusive social event for singles of all kinds. This is not a pressure-packed dating event — it’s a chance to connect, laugh, and meet new people in a welcoming, low-stress environment.
What to Expect: Casual mingling and conversation. Optional speed-dating rounds (participation is totally up to you. Light facilitation to keep things moving and fun. A mix of social, friendly, and flirty energy — no awkward expectations
Whether you’re newly single, happily single, or just curious to meet new humans, this night is designed to feel easy and enjoyable.
Important Note: This event will be filmed as part of a documentary project. All attendees are required to sign a likeness release in order to participate. If you’re not comfortable being on camera, this event may not be the right fit.

Bruin's Watch Party with Jameson Irish Whiskey
2026-03-07 13:00 - 15:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Join us 1:00-3:00pm at Island Pickle for a Boston Bruin’s Watch Party with Jameson Irish Whiskey. We’ll have lots of giveaways, swag, specials and more! The Tavern is a great place to experience the game!

Live Music with Michael Oakland
2026-03-07 17:00 - 20:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States

Live Music with J3 (Just the 3 of Us)
2026-03-27 19:00 - 21:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Come in and enjoy the music of Just the 3 of us (J3)

Live music with The Most Band
2026-03-28 18:00 - 21:00
Swing on down to the Island and enjoy The Most Band, a fun group that plays a danceable mix of rock and roll classics! It’s Rock and Roll like you remember it….

Saturday Night Live... at the Island
2026-03-28 19:00 - 21:00, 2026-04-04 19:00 - 21:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Looking for something new and fun to do on a Saturday Night? Come have fun on the Island for our Saturday Night Live event! Join us for a high-energy, open play night with music in a fun and lively social atmosphere. This is a 21+ event. Entry includes one drink ticket. Equipment rentals are available. Come learn or watch pickleball in a fun atmosphere, hang around for food and drink! Sign up using the Island Pickle app which is located on the homepage of Island Pickle

Cribbage Night at Island Pickle
2026-03-30 18:00 - 20:00, 2026-04-06 18:00 - 20:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Join us for a fun, friendly and FREE Cribbage Night at Island Pickle every Monday from 6:00-8:00pm. Open to the public and everyone is welcome. We’ll be playing a casual round-robin format where you’ll face multiple opponents and compete for the top spot of the night with the winner receiving a prize. Matches are quick, competitive, and perfect for a great evening out.
Open to the public so grab a friend (or two) and come enjoy some cards, laughs, and a little friendly competition. But seats are limited to the first 10 players who sign up. We’re playing in the Tavern so food (and drink) is available. See you at the tables!

Red Sox Opening Day Watch Party
2026-04-04 16:00 - 18:00
Let’s root, root, root for the home team at the Red Sox Opening Day Watch Party! Come on down to the Island and root on the Red Sox as they open the 2026 season on April 4, 2026 against the Cincinnati Reds. Kettle One vodka will be here with tastings and special drinks to get the season started. Chef Nick’s full menu will be available, and you can be sure he’ll have some special on the menu that day to celebrate Opening Day! First pitch is scheduled for 4:10, let’s Play Ball!
Make sure you join us for every Red Sox game in the Tavern the rest of the season.

Trivia with Lemonadio
2026-04-06 18:00 - 20:00
Join us for a fun night of trivia with Lemonadio! Bring your friends, make a team, win fun prizes!

Moving Day at the Masters
2026-04-11 13:00 - 19:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Saturday is moving day at the Masters… the day golfers jockey for position on the leaderboard, aiming to set themselves up for a chance at the winning the tournament and earning the coveted Green Jacket. Join us in the Tavern as we bring Augusta, GA to Mashpee with Masters-inspired food and drink, plus some special tastings and signature cocktails featuring Kettle One vodka. It’s a “Tradition Unlike Any Other”….so come to the Island and experience it!
