Experience Winter

So we survived the hustle, bustle, and heat of the summer season, and now we find ourselves on the other side, free from traffic and crowds but – nothing to do? Au contraire, hardy ones! The winter Island is too good to stay inside. Whether you’re in the mood to tuck into some hearty food, sit back and be entertained, or venture into the bracing outdoors, there are plenty of ways to get out and appreciate the other season.

1. Nights on the town. Vineyard restaurants offer a great escape from winter hibernation. The Monday night special at Offshore Ale Company in Oak Bluffs is popular November through mid-April, when you get two entrées for the price of one (including pizza!). The Wharf Restaurant in Edgartown is a hot spot on Wednesdays for trivia, as teams battle wits for first place and bragging rights (starts at 8 p.m., registration at 7:30). Atria in Edgartown hosts iconic Island jazz pianist John Alaimo on Friday evenings downstairs in its Brick Cellar Bar, where it also slings two-for-one burgers Sundays nights – though it may be switching what’s special throughout the winter (see Atria’s Facebook page for details).

2. Much ado about Shakespeare. The Bard will be laughing in his grave this winter as the ensemble cast of Shakespeare for the Masses tackles its fourth season of abridged, accessible, and absurdly funny renditions of Shakespeare classics. The troupe performs a lineup of six or seven plays over the season, which runs November through early May. Rehearsal time is minimal and the actors read directly from their scripts, which lends an off-the-cuff hilarity to the theatrical high jinks. In past years the Vineyard Playhouse has hosted the series but building reconstruction is sending the players elsewhere this season. For up-to-date info, join Shakespeare for the Masses on Facebook.

3. Bright lights. The days are getting shorter, but the holiday season lights up the Island. For high-voltage holiday illumination, don’t miss the over-the-top display at the Gatchell house on County Road in Oak Bluffs. Mark Crossland of Oak Bluffs puts his own special spin on the holidays each year, setting a floating Christmas tree adrift in the town’s Sunset Lake across from the harbor. Watch the Oak Bluffs tree lighting at Post Office Square between Circuit and Kennebec avenues on Wednesday, December 7, at 6 p.m. and the annual lighting of the Edgartown Lighthouse with treats outside the Harbor View Hotel & Resort on Friday, December 9, at 5:30 p.m.

4. Up-Island cinema. The Martha’s Vineyard Film Festival offers both a film series and a festival at the Chilmark Community Center this winter season. The series runs the first Saturday in December, January, and February, and includes Cinema Circus – short films from around the world geared toward children – as well as dinner and a feature film for adults. The festival returns for its twelfth season the weekend of March 16 to 18, offering a variety of award-winning films. Tickets for both events are available at the door or online at, along with schedule information.

5. Pond skating. Bitterly cold weather has one big plus: Some Island ponds freeze up enough for skating. Prime spots include Duarte’s Pond and Seth’s Pond on Lambert’s Cove Road, Mill Pond on Edgartown–West Tisbury Road, and Whiting’s Pond (also called Parsonage Pond) near Alley’s General Store, all in West Tisbury. Whether you’re of the triple-lutz, sticks-and-pucks, or pray-not-to-fall variety, lace up those skates for some old-school winter skating. Squibnocket Pond (in Chilmark and Aquinnah) and the great ponds, all brackish, sometimes freeze too; though the surface can be bumpy, the views are spectacular.