🎶 This Weekend on Martha's Vineyard: 9/19-9/21

Tivoli Day, MV Songwriting Festival, Kids Derby Day, 4 permanent closings, fall hikes + events for this month

We say goodbye to summer this weekend with farewells to local favorites, plenty for Derby fans, and lots of live music to close out the season.

⏱️ This Week on MVacay

🗺️ What To Do This Weekend

Friday, September 19, 2025

• 🎣 MV Striped Bass + Bluefish Derby / More Info

• 🎨Plein Aire MV and MVAA Members Art Exhibition at Old Sculpin Gallery, Edgartown, 10a–5p (Fri–Sun) / More Info

• 🎶 Martha’s Vineyard Songwriting Festival

  • Friday, September 19 – All-day performances in Oak Bluffs including Girls at the Sandbar, VIP hangouts, and Behind the Curtains at Strand Theatre.

  • Saturday, September 20 – Tivoli Day set, Rising Stars showcase at Strand Theatre, VIP hangouts, and After Party at Sandbar.

  • Sunday, September 21 – Brunch show in Vineyard Haven, Nashville Rising Stars in Falmouth, and evening sessions at Strand Theatre.

• 🎭 Mrs. Stern Wanders the Prussian State Library at MV Playhouse, Vineyard Haven, 7p (Sat too) / More Info

Saturday, September 20, 2025

• 🧺 West Tisbury Farmers Market at Agricultural Hall, 9a–12p / More Info / Free

• 🌅 Darkness into Vineyard Light Suicide Prevention Walk at Bend in the Road, Edgartown, 5–7a / More Info / $25

• 🏃 23rd Annual NAACP George V. Tankard Jr. Memorial 5K at Summercamp, Oak Bluffs, 9–11a / More Info / $25

• 🧘 Self-Care Saturdays at Felix Neck Wildlife Sanctuary, Edgartown, 9a / More Info /
  This wellness morning includes yoga, meditation, and time in nature—bring your mat and water.

• 🎉 Tivoli Day at Oak Bluffs, 10a-6p / More Info
  A beloved street fair with food, shopping, and entertainment to celebrate the end of summer season. Music starts at 12.

• 🌳 Oak Origins Lecture and Tour at Far Barn, West Tisbury, 10a–12p / More Info / $15
  Join a guided lecture and walking tour with oak expert Andrew Hipp, exploring centuries of research and PHA's living oak collection.

• 🏈 MVRHS Varsity Football Game vs. Sharon at MV Regional High School, Oak Bluffs, 1:30p / donations suggested

• 🎶 An Evening with Rising Stars at Strand Theatre, Oak Bluffs, 7–11p / More Info / $33.85–$995
  Hear Nashville's next generation of talent in this lively concert featuring new voices and big energy.

Sunday, September 21, 2025

• 🎉 Oak Bluffs Open Market at Washington Park, Oak Bluffs, 10a–2p

• 🖼️ Vineyard Artisans Summer Festival at Union Chapel, Oak Bluffs, 10a-2p / More Info / Free

• 🎣 Free Kid’s Day – MV Striped Bass & Bluefish Derby at OB Ferry Wharf, 6a / More Info / free
  Young anglers cast off early in this beloved annual Derby event for kids, held at the Oak Bluffs ferry wharf.

• 🖼️ Gone Fishing Opening Reception at Featherstone Center for the Arts, Oak Bluffs, 4–6p / More Info / free
  Celebrate fishing season and MV's Derby tradition with marine-themed art and light refreshments.

• 🎶 Community Sing at Tisbury Amphitheater, Vineyard Haven, 5–6p / More Info / free
  Join an all-ages, no-experience-needed group sing outdoors in the woods of Tashmoo Overlook.

• 🔥 Equinox Celebration and Bonfire at Native Earth Teaching Farm, Chilmark, 6–9p / / free
  Gather for potluck, firelight, and seasonal reflection in a family-friendly farm setting.

• 🌸 Family Flower Cut-Your-Own at Slough Farm, 4–5p (or 5–6p) / More Info / $10

• 🎶 Sundays in the Park Concert at Oak Bluffs Bandstand, 5:30-7:30p

⚠️ Events subject to change. Always check before you go!

Behind the Paywall: a beloved chef says goodbye, a major arts group pauses, a festival gets pushed again, and an Oktoberfest pop-up. Plus the usual community updates, standout classes, and save the dates you’ll want on your calendar.