It’s finally fall, friends!
⏱️ This Week on MVacay
I wrote out my annual fall list of favorite traditions and new additions for 2026:
It’s Derby Time, so I wanted to bring out my beginners guide to fishing on MV, and also in honor of the Shenandoah I found my sailing guide as well!
🗺️ What To Do This Weekend
Friday, September 18, 2026
🎨 Art Show and Sale to Support Habitat for Humanity @ Grange Hall, West Tisbury, 10a-6p (Sat too) / More Info / Free
Shop work by Island artists alongside secondhand art and a silent auction. Proceeds support Habitat for Humanity MV while also highlighting local artists.⛵ Shenandoah Parade of Sail @ Tashmoo Cove, Vineyard Haven, 12p / More Info / Free
Accompany the schooner Shenandoah as she leaves Tashmoo Cove on her final voyage. The sail kicks off a three-day community celebration marking the historic vessel’s return home.🌱 The Giving Garden: Fall Tour, Taste, and Take-Home with Roxanne Kapitan @ MV Public Charter School, West Tisbury, 4-5:30p / More Info / Free
Tour the school’s food forest and learn about perennial edibles and the basics of forest gardening. Participants can taste plants including pilgrim cranberries and sea kale and take home seeds or plant divisions for their own gardens.🖼️ Opening Reception: The Two Worlds of Denys Wortman @ Martha’s Vineyard Museum, Vineyard Haven, 5:30-7p / More Info / $20
🎶 Behind the Curtain With the Nashville Hit Makers @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$103.22
Nashville songwriters CJ Solar, Phil Barton, Joe Fox and Johnny Clawson perform songs they wrote for major country artists and share the stories behind them. Their credits include music recorded by Morgan Wallen, Blake Shelton, Kenny Chesney, Jason Aldean and others.🎭 Driver’s Seat: Obsessive Compulsive Disaster @ MV Playhouse, Vineyard Haven, 7p (Sat too) / More Info / Pay-What-You-Can
Written and performed by Ellie Brelis and directed by Leif Moore, this acclaimed solo show traces OCD, a breakup, hospitalization, coming out and recovery with dark humor and candor. The play was written during Brelis’s own 2020 mental health crisis and later performed at the Edinburgh Fringe Festival.🎬 Tony @ MV Film Center, Vineyard Haven, 7:30p (Sat 7:30p + Sun 4p) / More Info / $12
Saturday September 19, 2026
🌅 Darkness into Vineyard Light Suicide Prevention and Awareness Walk @ Bend in the Road, State Beach, Edgartown, 5-7a / More Info / $25
Participants gather before sunrise and walk through daybreak, symbolizing a passage from the darkness of depression and mental illness into hope and healing. Organizers say this will be the final edition of the annual event.🎉 Tivoli Day @ Circuit Avenue, Oak Bluffs, 10a-6p / More Info
Circuit Avenue turns into a daylong street celebration with food, local artists, shopping specials and family-friendly fun. Live music runs 12-6p at the Main Stage in front of Rockland Trust, Healy Square and The Ritz; rain date is Sunday, Sept. 20.🏃 24th Annual NAACP George V. Tankard Jr. Memorial 5K Road Race/Walk @ Summercamp Hotel + Ocean Park, Oak Bluffs, 9a-12p / More Info
⛵ Community Potluck Celebration of Shenandoah @ Black Dog Wharf, Vineyard Haven, 5-7p / More Info / Free
🎤 An Evening With Music City’s Rising Stars @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$135.23
Sunday September 20, 2026
🎣 Kid’s Mini Derby @ Steamship Authority Wharf, Oak Bluffs, 6-8a / More Info / Free
A special early-morning fishing event for kids ages 4-14, with prizes and no registration or Derby button required.🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free
🎨 Vineyard Artisans Festivals @ Grange Hall, West Tisbury, 10a-2p / More Info / Free
⛵ Shenandoah Open Boat Tours @ Black Dog Wharf, Vineyard Haven, 11a-5p / More Info / Free
🏈 Football and Yard Games @ Nomans, Oak Bluffs, 1-5p / More Info /
🎶 Community Sing @ Tisbury Amphitheater, Vineyard Haven, 5-6p / More Info / Free
🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free
🎸 Behind The Curtain: Sunday Edition with The Nashville Hit Makers @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$391.33
What’s New This Week on MV: Island updates, restaurant closings, new businesses, fall events and Save the Dates through October.