Daily through Sunday, Dec. 18, 12 to 4 pm
Featherstone’s 20th Annual Holiday Gift Show
30 Featherstone Ln., Oak Bluffs
A one-stop holiday destination with handmade gifts from Island artists, including paintings, photographs, pottery, crafts, jewelry, clothing, accessories, soaps, dog goods, ornaments, cards, calendars, and stocking stuffers. Closed Thanksgiving Day. For details, visit featherstoneart.org.
Daily through Saturday, Dec. 31, 5 to 8 pm
Gatchell Holiday Lights
County Road, Oak Bluffs
For more than 40 years, the Gatchell family has decorated their house with a massive Christmas light display, complete with reindeer, snowmen, and more than 20,000 sparkling lights. You are welcome to park your car and get out and walk around. You can also bring nonperishable food items or a monetary donation for the Island Food Pantry.
Friday, Nov. 25, and Saturday, Nov. 26, 10 am to 4 pm
Saturday, Dec. 17, 10 am to 4 pm
Vineyard Artisans Festival and Holiday Fair
Agricultural Hall (Nov.) and Grange Hall (Dec.), West Tisbury
Pick up unique holiday gifts created by Island artists at the Vineyard Artisans festival. There is something for everyone, including fine art, clothing, jewelry, ceramics, journals, cards, woodwork, baskets, and much more. For details, check vineyardartisans.com.
Saturday, Nov. 26
Crossland’s Christmas Display
Ocean Park, Oak Bluffs
Celebrate the start of the holiday season with Crossland Landscape’s annual lighting of decorations in Ocean Park. By sunset, bring the whole family to see the park come alive with a magical glowing scene. The lights will be on display every weekend through December.
Saturday, Nov. 26, 6 to 7:30 pm
Oak Bluffs Tree Lighting
Celebrate the holiday season with the annual lighting of the Oak Bluffs decorated tree in Healey Square. Grab some hot chocolate, candy from Enchanted Chocolates, and other refreshments, then put on reindeer antlers and enjoy hearing carols and seeing the town center light up for the holidays. For more information, visit obamv.com.
Saturday, Dec. 3, 7:30 pm, and Sunday, Dec. 4, 3 pm
Island Community Chorus’ Holiday Concert
Old Whaling Church, Edgartown
Get into the holiday spirit with a concert from about 65 members of the Island Community Chorus. The music repertoire will include a special arrangement by the new director, William Peek, of Robert Frost’s poem “Stopping by the Woods on a Snowy Evening.” Other songs are “The Christmas Song,” a Hanukkah song, Mendelssohn’s “Behold a Star from Jacob Shining,” and many others. To learn more, visit islandcommunitychorus.com.
Thursday, Dec. 8, to Sunday, Dec. 11
41st Annual Christmas in Edgartown
Experience quintessential small-town holiday shopping, with decorated storefront windows, an art and crafts festival, horse-drawn carriage rides, the lighting of the Edgartown lighthouse, a parade, a dog show, store specials, and much more. For the schedule, visit christmasinedgartown.com.
Friday, Dec. 9, 4 to 6 pm
Saturday, Dec. 10, 12 to 4 pm
Sunday, Dec. 11, 10 am to 2 pm
Teddy Bear Suite
Nevin Square, Edgartown
Enjoy seeing festive teddy bears of all shapes and sizes in the magical setting of the Nevin Square courtyard. They can also be found in their decorated holiday suite and photo studio at 29 Winter St. A suggested donation to visit with the bears and take fun photos benefits the M.V. Boys & Girls Club. For details, see mvteddybearsuite.com.
Saturday, Dec. 10, 10 am to 2 pm
Federated Church, Edgartown
Decorate gingerbread houses, make beeswax candles, and shop for holiday craft kits, children’s books, handmade toys, and other gifts. Also enjoy a warm lunch at the Elves’ Café. All proceeds benefit the Plum Hill School in West Tisbury. For more information, email firstname.lastname@example.org or call 508-696-7701.
Sunday, Dec. 18, 3 pm
M.V. Family Chorus’ 21st Annual Winter Concert and Community Sing
Milokan Cultural Center, Chilmark
Listen to songs of peace, hope, and light from the M.V. Family Chorus, directed by Roberta Kirn of Be Well Sing. The concert will be in-person at the Milokan Center on the Native Earth Teaching Farm. For those who want to join the chorus, there are rehearsals on Tuesday evenings. For details, visit bewellsing.com/events or email email@example.com.