December is an enchanting month to be on Martha’s Vineyard. Snowy hikes, holiday shopping, music, art, and more. Here are the highlights for enjoying December on the island. “Winter is the time for comfort, for good food and warmth, for the touch of a friendly hand and for a talk beside the fire: it is the time for home.” - Edith Sitwell
- Thanksgiving Art SALE: Sculptures, rugs, wall art and more! - Tom Galloway Collection. Extensive collection of sculpture, paintings, and more is for sale, $20 - $3000. Pick out a new piece for the garden, the mantel or your walls. 20% of all sales benefit the Island Housing Trust on Martha's Vineyard.
- Island Made Holiday Gift Show - Daily in December from 10:00am to 5:00pm at Heather Gardens. Featuring fifteen of your favorite Vineyard artisans. 377 State Road, West Tisbury, MA 02575.
- Louisa Gould Gallery Art Show: Small Wonders - Saturdays in December from 11:00am to 5:00pm. Annual art show of affordable smaller works by gallery artists Paul Beebe ASMA, Theresa Girard, Sally Martone, Wooley Dutton, Suzanne Hill, John Holladay, Donna Blackburn, Deborah T. Colter, Timothy Gillespie and Britt Bair. 54 Main Street, Vineyard Haven, MA 02568
- Salt Rock Chocolate Company Pop-Up - Wednesdays & Saturdays in December from 12:00pm to 4:00pm. Pre-assorted boxes, 5-pound limit. Will close early if chocolate sells out. 24 Basin Road, Menemsha, MA 02535
- ‘Tis the Season to Keep the Lights On - Fridays & Saturdays in December from 4:00pm to 6:00pm, Get in the festive mood with glittering street lights and falling snow during this season on magical Main Street and help support local businesses keep "the lights on" year round.
- 39th Annual Christmas in Edgartown - Throughout December. This year’s Christmas In Edgartown will take place with appropriate (and magical) modifications to continue Edgartown’s work of keeping our community safe, supported, and open for business. Our committee and local businesses are diligently working to re-imagine your favorite traditions, while navigating weekly and daily changes to our community’s needs and health. Our businesses and nonprofits need your support this year, so spend locally…enjoy Edgartown for some much needed 2020-style holiday cheer!
- 6th Annual Teddy Bear Trot - Virtual 5K & Fun Run - Sun December 6th - Sun December 13th.
- Docking Around the Christmas Tree - Thursday, December 10th at 10:00an through Sunday, December 13th at 6:00om. Dock Street, Edgartown. Come "Shop around the Dock" down on Dock Street with Sea Legs and Untameable Gallery! Enjoy complimentary roasted chestnuts, libations, polaroid photos with life-size Santa, free gifts with purchase, and sales from 15-50% off all weekend long! Drop off a letter to Santa in our special mailbox, belt out carols at 5PM daily, and revel in the Christmas spirit down at the shops by the water!
- Horse Drawn Carriage Rides with the Harbor View Hotel - Friday, December 11th at 11:00am through Saturday, December 12th at 2:00pm.
- Teddies Around Town Scavenger Hunt - Saturday, December 12th from 11:00am to 1:00pm. Elf on the Shelf is joining forces with Teddies Around Town to make a fun, safe, and meaningful self guided scavenger hunt with a cause. Elves will be Bears this year, and they will go from hiding on the shelves to hiding in storefront windows.
- Christmas Faire - Saturday, December 12 at 9:30am to 2:30pm. “An Island Christmas—a Celebration of Land and Sea” is this year’s theme with beautiful wreaths, swags and centerpieces with decorations from both land and sea, Christmas cards with vintage snowstorm photos of West Tisbury and the church. The raffle will feature a lovely Nativity Scene. We will take all precautions to ensure this a safe and yet festive event. First Congregational Church of West Tisbury, 1051 State Road, West Tisbury, MA 02575
- MET Opera Encore: Madama Butterfly - Saturday, December 12 at 1:00pm. Leading sopranos Hui He and Ana María Martínez share the heartbreaking title role of the doomed geisha, with tenors Piero Pretti and Bruce Sledge as the American naval officer who abandons her. Brazilian baritone Paulo Szot adds a new role to his Met repertory as Sharpless, a role that he has previously sung at Marseilles Opera. Pier Giorgio Morandi is on the podium for Anthony Minghella’s sweeping production, a perennial audience favorite.
- The Long Brickyard Hike - Sunday, December 13 at 1:00pm to 4:00pm. Explore the remnants of and learn about the historic 19th century brickworks on this afternoon hike led by Martha’s Vineyard stewardship manager David Bouck. Join us on this not-for-beginners hike to the iconic 45-foot chimney and take in the serenity of Roaring Brook. Trail follows uneven terrain on the way down, followed by a strenuous uphill hike on the way back. Water and water bottles, comfortable shoes and layers recommended. Masks a must. Meet at Menemsha Hills parking lot off North Road. Advance ticket purchase required; space is limited.