Help Oak Bluffs kick off the holiday season on Wednesday, Nov. 30, in Healy Square. There will be caroling with the Vineyard Classic Brass, the traditional Christmas tree lighting, and festive holiday music by the Brian Weiland Band. Guests can also enjoy plenty of hot chocolate, free antlers, and a visit from Santa. Bring a food item for the Island Food Pantry. The tree will be lit at 6:30 pm. For more information, visit oakbluffsmv.com.