Island Pickle

Maria & Den Duo
2026-04-24 18:00 - 21:00 (America/New_York) | MA
Come join us at the Island for Maria & Den, a husband and wife duo performing soft classic hits from the 60’s, 70’s, and today.

Beautifully Human Band
2026-04-25 18:00 - 21:00 | MA
Come listen to Beautifully Human – an acoustic musical trio consisting of Rowan Desautels, Richie Oliver and John Brittingham. Based in New Bedford, the group performs and array of cover songs and some of their original music.

Saturday Night Live... at the Island
2026-04-25 19:00 - 21:00, 2026-05-02 19:00 - 21:00, 2026-05-09 19:00 - 21:00, 2026-05-16 19:00 - 21:00, 2026-05-23 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
2026-04-27 18:00 - 20:00, 2026-05-04 18:00 - 20:00, 2026-05-11 18:00 - 20:00, 2026-05-18 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!

Cornhole Tuesdays with Mixed Nuts
2026-04-28 18:00 - 21:00, 2026-05-05 18:00 - 21:00, 2026-05-12 18:00 - 21:00, 2026-05-19 18:00 - 21:00 | MA
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!

Line Dancing on the Island
2026-04-29 18:00 - 20:00, 2026-05-13 18:00 - 20:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Join us for a fun night of Line Dancing Night with Paula. Whether you’re a seasoned dancer or brand new, enjoy great music, and share a night of laughs with friends. Grab a drink, follow the beat, and dance the night away! $5 at the door to be part of the fun! Let’s get up and dance!

Live Music with Good Question
2026-05-01 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States

Kentucky Derby Watch Party
2026-05-02 16:00 - 20:00 | MA
Join us on the Island for the Kentucky Derby Watch Party!
Bulleit Bourbon will be here from 4:00-6:00pm with tastings, special cocktails, swag giveaways and lots more fun. Dress in your best Kentucky Derby-inspired outfits and compete in our “Best Dressed” awards. Island Pickle will be running other Kentucky Derby-inspired food and drink specials. Get in the Island Pickle Kentucky Derby “Blind Draw” pool for a chance to win prizes!

Live Music with Eddie Crownshaw
2026-05-02 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States

Live Music with Your Favorite Color
2026-05-08 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Playing all your R&B, Pop and Classic Rock favorites! Lead vocalist-Duke Jones, Bassist-John Pina, keyboardist-Lou Dutton, Drummer-Dave Perry and Guitarist- Tom Anger. They keep you entertained!

Live Music with Flydown
2026-05-09 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Brian Kerins and Flydown cover all genres of music to keep you entertained all night!

Island Pickle Members Dinner
2026-05-14 18:00 - 21:00 | MA
SAVE THE DATE
Join us for our inagural Island Pickle Members Dinner. This all inclusive dinner will feature a 3 course, island inspired menu from Chef’s Nick and Shane. Pricing, tickets and reservations to come shortly – stay tuned!

Riptide Band
2026-05-15 18:00 - 21:00 | MA
Get ready for an unforgettable night of live music as Riptide Band rocks Island Pickle! Known for their high-energy performances and crowd-favorite covers, Riptide brings the perfect mix of beachy vibes and dance-worthy hits.

Celebrate the Patio at Island Pickle Opening
2026-05-16 16:00 - 18:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Join us in celebrating the grand opening of the Patio at Island Pickle Patio on May 16, 2026! Located just outside the 4-pack pickleball courts, our new covered outdoor patio features a dedicated bar, bar seating, table seating, cozy fire pits, and casual lounge areas. With court doors opening directly onto the patio, it’s the perfect place to relax after a match or gather with friends and family. Enjoy great food, fresh air, and a vibrant atmosphere all season long – from Spring through Fall. Like the Tavern and the rest of our facility, the Patio at Island Pickle is open to the public. The grand opening will feature tastings of Hight Noon and Lucky Dog ready to drink cocktails, along with some fun, music and giveaways!

High Noon & Lucky One Promo
2026-05-16 16:00 - 18:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Join us for an exciting High Noon and Lucky One Lemonade Tasting Event. Sip, sample, and discover your new favorite drink while soaking up the island vibes. Whether you’re a fan of light and bubbly or sweet with a twist, this tasting has something for everyone. Bring your friends, enjoy great company, and experience a lineup of summer-perfect beverages.

Gracie Grace and all the Goodboys
2026-05-16 18:30 - 21:30 | MA
Gracie Grace & All The Goodboys are bringing back an era of music that once seemed lost. A blues inspired, soulful pop/rock band that was raised on good old fashioned, down right funky rock and soul, they are no stranger to getting down with the dirty, lost in the sauce, confused in the groove, locked in the rock, and entranced in the dance.

Pickleball for Parkinson's
2026-05-17 15:00 - 17:00 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
FREE Fun, Fitness and Friendship! Instruction and supervised Open Play for individuals with Parkinson’s who are steady on their feet. Pickleball aids Parkinson’s patients by improving balance, hand-eye coordination, and visual-spatial awareness. Wear court shoes, equipment provided. Contact Nat@islandpickle for more information.

Miss Julia Violet Band
2026-05-22 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Playing a mix of covers and original music, Miss Julia Violet band is a souful mix of musicians who will keep you on your feet all night long!

Live Music with Dial Up
2026-05-23 18:30 - 21:30 | Island Pickle, 51 Evergreen Circle, Mashpee, MA, 02649, United States
Dial Up is a high energy rock and roll band covering the hits from the 90’s and 2000’s that will keep you rocking all night long!
