🎃 This Weekend on Martha's Vineyard: 10/31-11/2

halloween options - trick or treat, on the hill, haunted house, best fest parade, running routes + community support

Hello all! It’s been a heavy week in the news, and if you or someone you know could use support, my Support Services Guide outlines where to find help with food access on-Island. You can also read my in-depth post on the Island Food Pantry. There are compassionate, community-driven programs here to help 🧡

⏱️ This Week on MVacay

🗺️ What To Do This Weekend

Friday, October 31, 2025 - Halloween

• 🎃 Howl-a-ween Bark and Boo Bash at MV Chamber of Commerce, 12–5p / More Info / Free

• 🎃 Halloween Party at West Tisbury Library, 3–5p / More Info / Free

• 🎃 Annual Chilmark Kids Halloween Party at Chilmark Community Center, 5–8p

• 🎭 Vineyard Haven Halloween Puppet Parade 2025 at Main Street, Vineyard Haven, 4–4:30p / Free

• 👹 Haunted House at MV Screenprinting, 426 State Road, Vineyard Haven, 4–10p / $10 Adult, $5 Child (10 and under)
  Kid-friendly walkthroughs happen from 4–5:30p, with a scarier “lights-out” horror mode from 7–10p. Costumes encouraged!

• 👻 Main Street Trick-or-Treat & Costume Contest at Vineyard Haven, 4:30–5:30p
  Visit local businesses for trick-or-treating, enjoy a live DJ and costume contest by the Capawock, plus raffles with Tisbury EMS.

• 🍬 Halloween on the Hill at MV Museum, 4:30–6p / More Info / Free
  Families can enjoy trick-or-treating, crafts, and games throughout the museum with a sensory-friendly space for all ages.

• 🕯️ Spirits & Spirits: Hotel Le Grangé at Grange Hall, West Tisbury, 6:15p & 8p / More Info / Pay-what-you-can
  Circuit Arts presents a haunting immersive theater experience in a historic setting where the audience meets ghosts of the past.

• 💃 Dance Party for Habitat for Humanity at PA Club, Oak Bluffs, 7–10p / More Info / $20 Suggested Donation
  A festive fundraiser with live music by Serendipity, costume contests, a silent auction, and a fly-away raffle for a Boston getaway.

• 🎭 Ritz Halloween Costume Contest at The Ritz, Oak Bluffs, 8p–late

• 🪩 Disco Horror Night at Alchemy Bistro & Bar, Edgartown, 10p

Saturday, November 1, 2025

• 🌽 Harvest Festival at Oak Bluffs Public Library, 10a–12:30p / More Info / Free
  Celebrate local farming with cider pressing, vegetable printing, and fall games on the library lawn in partnership with Slough Farm.

• 👻 Haunted Edgartown Ghost Tour at 58 North Water Street, Edgartown, 6–7:30p / More Info / $20

• ☕ Scream In Your Coffee? at Mocha Motts, Oak Bluffs, 6–7p / Free
  Watch a chilling 15-minute dance and storytelling performance unfold from the street through the café’s front windows.

• 🎷 The Best Fest Parade at The Strand Theatre, Oak Bluffs, 7–8p / More Info / Free
  The Upis Land Band leads a second-line-style Halloween parade through Oak Bluffs with music, costumes, and community flair.

• 👑 Halloween Drag Show (Birdcage Bash) at Red Cat Kitchen, Oak Bluffs, 9p / Tickets / $40-55

• 🎸 Skatepark Fundraiser Show at MV Skatepark, 3p / Free (Donations Appreciated)
  Live punk and rock sets from to raise funds for the skatepark, costumes optional.

Sunday, November 2, 2025

• 🎶 B-Side Brunch at First Light Café at MV Museum, Vineyard Haven, 11a–2p / More Info / Free
  Enjoy soulful live music, great food, and a chance to explore the museum’s newest exhibits during this relaxed Sunday brunch.

• 🎶 Music Street Concert: All Kinds of Love at West Tisbury Library, 3–4p / More Info / Free
  Soprano, tenor, and pianist perform works inspired by love, art, and Broadway in this free classical concert open to all.

• 🎬 Bruce Springsteen: Deliver Me From Nowhere at The Strand Theatre, Oak Bluffs, 6–8p / More Info / $12