Karen M. Overtoom Logo
Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832

The Best of August on Martha's Vineyard


Finally, the summer we have been waiting for! The Fair, Live Music, Art Strolls. August is pack-full of adventure and fun. The Vineyard is waiting for you! Here are some of our favorites things to do this month on the island. 

  • Sunday, August 1 at 8:45am - Amity Island 5K & Fun Run - Lace up those running sneakers and join Amity Island Running Club for their annual 5K and fun run. Registration begins at 7:30 a.m., and the fun runners’ kickoff is at 8:45 a.m. 5K runners and walkers begin at 9 a.m. The race begins at the FARM Institute in Katama, and continues along Edgartown Bay Road, past South Beach and back along the bike path to the finish line at the FARM Institute. In-person and virtual options available.
  • Tuesday, August 3 from 8:00pm to 10:00pm at Trinity Park Tabernacle - Kate Taylor's Album Release: Why Wait! -   Kate Taylor and her producer, the famed musician, member of the British singing duo Peter and Gordon and 3 time “Producer of the Year” Grammy Award winner Peter Asher have teamed up once again for a new album collaboration, Why Wait!, set for release on August 6, 2021 on Red House Records/Compass Records Group.
  • August 1st – 5th - Shakespeare for the Masses: Quick & Painless & Free! - MACBETH - Tuesdays at Tisbury Amphitheater, Thursdays at other locales *
  • August 6th – 14th - African American Film Festival - The Run&Shoot Filmworks - Martha's Vineyard African American Film Festival also known as "The Summer's Finest Film Festival" is now entering its 19th year on Martha's Vineyard. They have screened and promoted some of the most outstanding and emerging Feature, Documentary and Short films produced by and starring African Americans from across the world.
  • Saturday, August 7 from 11:00am to 5:00pm & Sunday, August 8 from 9:30am to 3:00pm - Martha's Vineyard Book Festival 2021 Summer Series - The Martha’s Vineyard Book Festival will launch a live Summer Series this summer. Held both down-Island and up-Island, and outdoors, the Summer Series will feature 20 of the country’s leading authors speaking over three days. All events will be ticketed in advance and ticket sales will include the purchase of the book.
  • Saturday, August 7 from 4:00pm to 7:00pm - Art District Stroll - View artwork at Alison Shaw Gallery, Crossroads Gallery, Galaxy Gallery, Knowhere Art Gallery, Lucinda Sheldon Enamels and Periwinkle Studio.
  • August 8th-18th from 10:00 to 5:00 pm - Art Show: 50th Anniversary Show at the Field Gallery! This year, we celebrate our artists with a 3D Virtual Gallery Tour. We are not hosting our traditional artist cocktail receptions. All new work will be featured for two weeks and available for sale through the season in-person and online. Social distancing protocols are in place. We are happy to make accommodations to ensure your visit with us is comfortable. If you are not vaccinated, we ask for you to wear a face mask inside the Gallery to respect our fellow guests.
  • August 19th - 22nd from 10:00 am to 11:00 pm - THE FAIR! It’s the 159th Annual Martha's Vineyard Agricultural Fair! The annual Martha's Vineyard Agricultural Fair runs from August 19 through the 22 at the fairgrounds in West Tisbury. Rides, games, shucking and fiddle contests, skillet toss and livestock shows.  
  • Sundays & Fridays in August from 9:30am to 11:00am - Morning Stand Up Paddle Board Tours - Experience the beauty and serenity of the morning on Martha's Vineyard via paddleboard. Call or email lars@kismetoutfitters.com to RSVP or to inquire about rentals or private tours.
  • Sundays in the Park from 6:30pm to 8:30pm at Ocean Park - Aug. 1: John O'Toole Band, Aug. 8: Vineyard Haven Band, Aug. 15: Mrs. Biskis, Aug 22: Vineyard Haven Band, Aug. 29: The Jaywalkers
  • MV Concert Series at the Loft! - Live music is BACK!!! 8/1 Luna, 8/4 Dwight 7 Nicole, 8/5 Ripe, 8/6 Entrain, 8/7 Joan Osborne, 8/11 & 8/12 Badfish, 8/17 Dalton & The Sheriffs, 8/20 Martin Sexton, 8/24 G. Love & Chuck Treece, 8/25 Sammy Rae & The Friends, 8/27 The New Motif, 8/28 Livingston Taylor, 8/31 Dalton & The Sheriffs!