Harvest Festival - Saturday, November 1st from 10:00am to 12:30pm - Come celebrate Fall and the Vineyard’s agricultural roots! The Oak Bluffs Public Library is hosting our annual Harvest Festival in partnership with Slough Farm. All ages will enjoy the festivities outdoors on the library’s south lawn. There will be a lamb, cider press demonstrations, harvest vegetable printing, sack races, temporary tattoos and more! Popcorn and apple cider will be served.
Scream In Your Coffee? - Saturday, November 1st from 6:00pm to 7:00pm - A Circuit Avenue mainstay reveals its darker side before Best Fest. This 15-minute repeating performance, viewed from the outside looking in, is part dance, part storytelling, and wholly unsettling.
The Best Parade - Saturday, November 1st from 7:00pm to 8:00pm - Get ready - The Upis Land Band, our island’s very own second line parade band, is back and marching through Oak Bluffs with special guest performers! Come join the fun in your favorite Halloween attire and get ready for music, dancing in the street, and a bit of good old-fashioned shenanigans.
Mending Night with Dalila Bennett - Tuesday, November 4th from 5:30pm to 7:30pm - Led by Dalila Bennett of Fire Cat Farm. Are your Carhartt's looking a little worse for wear? Are your sweaters full of holes? Bring all your old and worn-down clothes to the Ag Hall and we’ll learn to mend them together! Dalila will demonstrate visible mending by hand and needle felting (for wool items). They will also be on-hand with a sewing machine for more difficult projects, like larger patches and thick fabrics. COST: FREE and open to all, registration appreciated but not required.
Sweet & Salty: Bay Scallops Abound - Thursday, November 6th from 5:30pm to 7:00pm - Learn how to identify a harvestable adult bay scallop. Then prepare this Vineyard holiday staple multiple ways with Chef Charlie Granquist from Slough Farm. Unlock the mysteries of the perfect pan-sear or a delicate crudo. Enjoy a family-style meal with winter harvests from land and sea. This program is for adults.
Bow Workshop Wreath Festival - Friday, November 7th from 3:00pm to 6:00pm - Help make the bows to go on the 55 wreaths to be sold at the Wreath Festival on Dec. 4th. Free. No experience needed. Sale proceeds benefit the Federated Church Minister's Discretionary Fund to help islanders in need.
Truckin' MV - Saturday, November 8th from 10:00am to 1:00pm - Mark your calendar! Vineyard Montessori School will hold the 12th annual Truckin’ MV free community event on Saturday, November 8th, from 10 a.m. to 1 p.m. at the MV Regional High School parking lot. Come for the trucks but stay for the fun-filled activities that make this a family affair - kids’ music, face painting, and crafts! Food will be available for purchase at the event. This is a free, all-ages event open to the public.
Barn Raisers Day - Saturday, November 8th from 1:00pm to 2:30pm - To celebrate the 31st anniversary of our community barn raising, we are building tiny Ag Halls! Visit the Ag Hall to enjoy snacks and warm drinks while working to construct a barn of your own—a model of the Ag Hall built from cardboard, craft supplies, play-doh, legos, and more! All materials will be provided (although you are welcome to bring your own!). This event is for all ages. Entries will be displayed at the Barn Raisers Ball, where people will vote for their favorite entry, and winners will receive a free 2026 Ag Society membership! COST: FREE and open to all, no registration required.
Barn Raisers Ball - Saturday, November 8th from 7:00pm to 10:00pm - We're excited to dance the night away with you all to celebrate the 1994 construction of our barn by over 300 community members! 31 years later, community still makes all our work possible, and we can't wait to celebrate with you all. Like past years, this will be a BYOB event with a dessert potluck and music by Johnny Hoy and the Bluefish.
Second Sunday Jazz Concert - Sunday, November 9th at 2:30pm - Featuring the Jeremy Berlin Trio with special guest Lucas Ostinato. A tribute to the great Brazilian composers.
A Harvest Tea Party with Indigenous Roots - Sunday, November 9th from 3:00pm to 4:00pm - Join Herring Pond Wampanoag Tribal member Taylor Smalley for a thoughtful exploration of the indigenous cranberry history and its enduring connection to Wampanoag traditions. Discover how this native fruit has shaped both ecology and community on Martha’s Vineyard—from its ancestral uses and symbolism to the development of local cranberry bogs. As part of this experience, enjoy a cup of locally harvested Cranberry Mint tea, accompanied by seasonally inspired baked goods, a vibrant reflection of the season’s transition from harvest to winter rest.
Naptime with David Stanwood - Thursday, November 13th & Friday November 28th from 3:30pm to 4:30pm - Experience the calming effect of harmonic vibration, with pianist and acclaimed piano technician David Stanwood. Naptime is a meditation hour. David’s piano improvisations expand and slow down time—allowing space for unwinding, resting, dreaming, writing, drawing, and meditating. Yoga mats and cushions are provided.
Heartwood Trio: The Well Tree - Friday & Saturday, November 14th & 15th at 7:00pm - Heartwood Trio presents The Well Tree, a lush, heart-tending musical experience that weaves song, story, and inspiration from the natural world. The group creates original compositions born from time spent in wild places, blending melody, rhythm, and allegorical storytelling to guide audiences on a journey of reflection, connection, and joy. Rooted in both emotional depth and imaginative creativity, the performance invites audiences into an experience that is immersive, transformative, and uniquely its own.
Minnesingers Silent Auction and Karaoke Fundraiser - Saturday, November 15th from 6:00pm to 9:00pm - Auction opens at 6 PM, Minnesingers perform at 7pm, Karaoke starts at 7:30pm. Join us for an unforgettable evening celebrating Martha’s Vineyard’s own Minnesingers! This special Fundraiser, Silent Auction & Karaoke Night will help send our talented student singers on their Performance Tour of Italy. Sing your heart out at karaoke! Enjoy light bites from Quitsa Kitchen, drinks are available for purchase
Live from the Grange: Victoria Cardona - Wednesday, November 19th at 7:30pm - Victoria Cardona is a guitarist, vocalist, and multi-instrumentalist one-woman band whose live looping performances create a sonic and visual journey through intricate layers of guitar, bass, percussion, and vocal harmonies. Rooted in her Cuban heritage and spanning jazz, blues, soul, Afro-Cuban, Afro-Caribbean, salsa, and rock ’n’ roll, Cardona fuses rhythm and harmony to deliver performances that are both technically impressive and deeply emotive. Her spontaneous, improvisational style invites audiences into an experience that is bold, playful, and utterly captivating.
Discover Your Family History - Saturday, November 22nd from 1:30pm to 2:30pm - Explore the past, connect with your ancestors, and uncover the stories that make your family unique! Join us for a discussion about genealogy where we provide guidance to help you trace your family history and build your family tree. Whether you're just beginning your genealogical journey or looking to dig deeper into your family roots, our program offers a quick guide on Ancestry.com Library Edition to help support your research.
Fall Festival - Friday, November 28th from 10:00am to 2:00pm - A festive celebration of fall at Felix Neck. With live animal shows, hayrides, crafts, food, and wreath making, there is fun to be had by the whole family!
Light Up Oak Bluffs Tree Lighting - Saturday, November 29th - Oak Bluffs celebrates the start of the Christmas season.
Trivia with Johnny Showtime - Tuesdays in November at 7:00pm
Karaoke with Johnny Showtime - Tuesdays in November at 9:00pm
Adult Board Game Night - Wednesdays in November from 7:30pm to 10:00pm - Adults are welcome to join us at the Barn and Bowl Bistro at 13 Uncas Ave, Oak Bluffs, MA 02557 for a variety of board games and socializing. We meet weekly at 7:30pm, and newcomers are always welcome.