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

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

Oct 30, 2025

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 🧡

In the name of equity and generosity, today’s full post is FREE!

⏱️ This Week on MVacay

🏃‍♀️Top Running Routes on Martha’s Vineyard

Lis from MVacay

Oct 27

🏃‍♀️Top Running Routes on Martha’s Vineyard

This guide includes 10 favorite routes on paved roads. I do my best to include distances, hilliness, surfaces, views, and where to park. It also rounds up annual races by month!

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🗺️ 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

📍MVacay’s Island Updates

⭐ New Offerings:

Zombie Crawl returns to Oak Bluffs today, Oct. 30 at 7 PM. Expect 50+ undead revelers shuffling from Sharky’s to The Ritz for zombie cocktails and a late-night dance party.
Cranberry Bog Tours: Pick your own cranberries at the Island’s only commercial bog! Tours run Sunday, Nov. 9 and Saturday, Nov. 15, 1–2 PM @ 572 Lambert’s Cove Rd, Tisbury ($10). If those times don’t work, drop by for self-guided picking Oct. 30–Nov. 25. Open most afternoons and weekends for $10 unlimited picking.
Harbor Homes will reopen the Island’s only overnight winter shelter on Nov. 1 at 111 New York Ave. in Oak Bluffs, offering meals and beds nightly through April.
Community Drive: Starting tomorrow, Rockland Trust branches across the Island will collect new and gently used winter coats for kids and adults through Jan. 10. Drop off donations during branch hours (8:30 AM–4 PM) to help keep local families warm this season.

📖 Island News:

The Island Cup (vs. Nantucket) has been called off this year after MVRHS’s football team ended its season early due to a shortage of healthy players.
Steamship Authority fares will rise about 5% (starting 1/1/26) across the board for standard car trips for visitors go up $6 each way in summer, passenger tickets rise 25¢–$1, and Islander excursion fares increase $1.75 in winter.

⏳Restaurant Updates:

Closing Soon: You Enjoy My Vegan Food Truck (10/31), Mad Martha’s (10/31), Tigerhawk Sandwich Co. (10/31), 19 Raw Oyster Bar (11/1), Net Result (closing for renovations 11/2-4/1), L’Etoile (11/15), The Pawnee House (11/30), Fat Ronnie’s Burger Bar (11/30)
Closed for the Season: See Off-Season Listings Here (updated yesterday)
Thanksgiving Pre-Orders: Beetlebung Farm, North Tabor Farm, The Maker, Morning Glory Farm, Scottish Bakehouse, 9 Craft Kitchen, Fish House.