Holiday Happenings

Santa enjoys the Edgartown Christmas Parade from a vintage firetruck.

Welcome to Holiday Happenings, a guide to Island-wide festivities to help make the holiday season easier to plan for. We’ve rounded up as many holiday events as we could find, and highlighted some we thought readers would like. In addition to events, you’ll find a roundup of holiday shops and pop ups (Page 9), a look at some of the longstanding Christmas in Edgartown traditions (Page 4), and a new New Year’s Eve offering to ring in 2020 (Page 12). For those curious about Christmas masses and church schedules, there’s a guide on Page 10. And on Page 6, read the story behind the illuminated light display you’ve no doubt seen around the gazebo at Ocean Park. We hope you find this Holiday Happenings guide useful, and email us at with any comments or suggestions. Happy holidays!

Ongoing events
Dec. 12- Jan 5
Crosslands Annual Christmas Displays
Ocean Park, Oak Bluffs
Crosslands annual Christmas displays and light/music show. Tune to 88.5 FM Friday through Sunday from 5 to 8 pm for a combo show.

Dec. 12-15

Christmas in Edgartown
All day, various Edgartown locations
Celebrate the 38th annual Christmas in Edgartown weekend with events for the entire family. More than 100 Edgartown and Island businesses participate in the festivities, and events and sales help raise over $50,000 for Island-wide charities and nonprofits. For more information, visit (See Pages 4 and 5 for a full list of events and details.)

Dec. 12-15
Featherstone Holiday Gift Show

Featherstone Center for the Arts, Oak Bluffs
Fun holiday shopping featuring affordable gifts made by Island artists. All gifts made on Martha’s Vineyard. Open daily.

Dec. 12-24
Vineyard Holiday Gift Shop
68 Lagoon Pond Road, Vineyard Haven
The Holiday Gift shop features many of your favorite Island artisans and craftspeople under one roof. Open daily. 

Dec. 16-24
Island Made Holidays
10 am – 6 pm, Alley’s Farm Stand, West Tisbury
Over 13 Island artisans feature homemade jams, wampum jewelry, herbal remedies, wooden and ceramic bowls and plates, felted animals, books, honey, and much more. 

Dec. 13-15

Teddy Bear Suite
10 am-8 pm; 10 am-4 pm; 10 am-2 pm; 17 Winter St., Nevin Square, EdgartownThe Teddy Bear Suite brings stuffed bears of every size and shape, decked out in their holiday finest, to Nevin Square in Edgartown. The fundraiser is a magical holiday tradition where family memories are made, and the money raised goes to the Martha’s Vineyard Boys And Girls Club.

Dec. 13-24
Gift of Art: Island Art Show
10 am-5 pm, the Carnegie, Edgartown
Discover works from 10 Island artists. Perfect for your home or as a special gift for a loved one. The small works are sure to charm one and all. 

Weekends through December

Holiday Open House
11 am-4 pm, Sargent Gallery, Aquinnah
Explore the current exhibit while enjoying local cider, wine, and cheese.

Island Alpaca Holiday Open House
10 am-4 pm, Island Alpaca, Vineyard Haven
Unique experience including a gift shop filled with locally grown garments, and down on-the-farm furry fun.

Daily events

Thursday, Dec. 12
Christmas in Edgartown
All day, various Edgartown locations. See page 5 for a full list of events, or visit

Christmas Faire Workshop
9 am- 4 pm, First Congregational Church of West Tisbury
Create wreaths and arrangements to sell at this annual fundraiser. Guidance available from experienced elves. Bring lunch and your own pruners if possible.

Christmas Greens & Centerpiece Making
3-5 pm, Chilmark Community Church
Make your own Christmas greens and centerpieces.

Friends and Family Night
5- 9 pm, Rainy Day, Vineyard Haven
Sip, shop, and save on an evening of early-buy holiday specials and giveaways. 

Thirsty Thursday Santa Run
5:30 pm, Bad Martha Farmer’s Brewery, Edgartown
Amity Island Club is teaming up with Edgartown Meat & Fish to host a festive run. Santa hats, beards, and glow necklaces will be provided. Bring a headlamp. Stay afterwards for beer at the brewery.

Holiday Art Party
6-8 pm, Jazen’s Art Studio, Oak Bluffs
Learn how to paint “Christmas Bench” while listening to music. Bring your own drinks and snacks.

Gift of Art Show Opening Reception
6-8 pm, the Carnegie, Edgartown
Discover your next favorite work of art. 

Sip, Script & Shop
6:30-8 pm, Citrine x Trust Shop, Vineyard Haven
An introduction to modern calligraphy with a pointed dip pen and ink.

Friday, Dec. 13
Christmas in Edgartown
All day, various Edgartown locations. See page 5 for a full list of events, or visit

Wreaths Across America
10 am, Oak Grove Cemetery, Vineyard Haven.
An event to honor those who have fallen and served.

Holiday Pop-Up
4-7 pm, Driftwood Jewelry, Oak Bluffs
Featuring Indian Hill Wampum and Lightship Bracelets.

Town Holiday Party
6-8 pm, Agricultural Hall, West Tisbury.
Potluck and party. Free. All are welcome.

Minnesingers Concert
8-10 pm, Old Whaling Church, Edgartown
The Island’s high school choral group performs a concert of seasonal favorites. 

Saturday, Dec. 14
Christmas Faire
9:30 am-2:30 pm, First Congregational Church, West Tisbury
Decorate your home with hand-crafted holiday decoration and pick up gifts for friends and family. Homemade baked goods and entertainment. Lunch served at 11:30 am. Christmas basket raffle.

Winter Arboretum Walk
10 am, Polly Hill Arboretum, West Tisbury
Join PHA staff for a look at plants of interest in the winter landscape. 

Handmade from the Heart
10 am-3 pm, Dr. Daniel Fisher House, Edgartown
Handmade from the Heart for Hospice includes jewelry, pottery, needlepoint, knitted items, baked goods, and other items for sale. 

Plum Hill School Annual Elves Faire
10 am-3 pm, Federated Church, Edgartown
Crafts, decorate a gingerbread house, silent auction, holiday gifts, delicious hot food and drink.

27th Annual Christmas in Edgartown Art and Crafts Fair
10 am-4 pm, Edgartown School
27th Annual Christmas in Edgartown Arts and Crafts Fair featuring the work of over 40 Island artists and craftspeople.

West Tisbury Farmers Market
10 am-1 pm, Agricultural Hall, West Tisbury
Locally made products, produce, meat, and more. Great gift finds.

Christmas in Edgartown Parade
11 am, Downtown Edgartown
Floats, animals, music, dancers, kids, fire engines, and of course, Santa. 

Poinsettia Sale
12-3 pm, Edgartown library
Poinsettias and unique gift items for sale to support the Edgartown library.

1-2 pm, Chilmark library
Wrap presents for winter holidays, winter birthdays, or just because. Winter tunes and cookies provided.

The Nutcracker and the Mouse King Ballet
3 pm, Edgartown library
For the holidays, a beautiful and fun adaptation of Tchaikovsky’s holiday favorite, performed by the Dutch National Ballet, with Matthew Golding.

Minnesingers Concert
4-6 pm, Old Whaling Church, Edgartown
The Island’s high school choral group performs a concert of seasonal favorites. 

Fundraising Dinner
5:30-8:30 pm, Lambert’s Cove Inn, West Tisbury
Woods and MV Teddy Bear Suite are teaming up to raise money for the Boys & Girls Club program “Healthy Happy Kids” by hosting a fundraiser dinner at the Lambert’s Cove Inn restaurant.

Holiday Party
7 pm, the Ritz, Oak Bluffs
Christmas music with Rosie Guerin and Sean McMahon followed by DJ Ricky Prime. Food by the Good Farm.

Sunday, Dec. 15

Santa at the Light
9-11 am, Cape Poge Wildlife Refuge, Chappaquiddick
Celebrate the season with a festive refuge ride and hot chocolate with Santa at the remote Cape Poge Light. Registration required. Email

Teddy Bear Trot 5K and Fun Run

9:30-11:30 am, Martha’s Vineyard Boys & Girls Club, Edgartown
Teddy Bear Trot Holiday 5K & Fun Run – dress in festive attire; an in-town course, part of the MV Teddy Bear Suite, a Boys & Girls Club fundraiser. 

Chilmark Holiday Flea Market

10 am-4 pm, Chilmark Community Center, Chilmark. Items for sale include holiday crafts, fresh holiday centerpieces, jewelry, scarves, clothing, collectables, candles and antiques. 

5th Annual Carol Sing
2-3 pm, Federated Church Meetinghouse, Edgartown. Free sing-along of your favorite Christmas Songs led by Peter R. Boak. Light refreshments to follow. Part of Christmas in Edgartown. Free.

Holiday Open House
2 pm, Tisbury Senior Center, Vineyard Haven
Featuring Susan Klein,f storyteller, with folklore memories of past Christmases. DJ Donald Rose will provide music. Door prizes.

Offerings of Music and Light
5 pm, Chilmark Community Church
Lia Kahler leads Island singers, musicians, dancers, and readers in free programs to brighten dark days. Carols, candle lighting, and refreshments. 

Monday, Dec. 16

Monday Night at the Movies: Holiday Affair
7 pm, Martha’s Vineyard Playhouse, Vineyard Haven.
Directed by Don Hartman, with Robert Mitchum and Janet Leigh.

Reflections of Peace Christmas Concert
7:30-9:30 pm, Old Whaling Church, Edgartown.
A Christmas concert to honor and benefit Hospice of MV. Contemporary, classical, holiday music.

Tuesday, Dec. 17

Martha’s Vineyard Family Chorus
6 pm, Martha’s Vineyard Hebrew Center, Vineyard Haven
Songs performed from around the world.

Holiday Movie and Gift Wrapping
7-8:30 pm, Vineyard Haven library
Wrap your Christmas gifts with a holiday movie playing in the background.

Wednesday, Dec. 18

Build Club: DIY Ornaments
3:30-5:30 pm, Vineyard Haven library
Make holiday ornaments. Best for kids 8 to 12 years old.

Friends and Family Night
5-9 pm, Glass House, Vineyard Haven
Shop and enjoy holiday cocktails, special discounts, and a holiday raffle.

Advent Evensong Services
5:30-6:30 pm, First Congregational Church of West Tisbury
Three Contemplative Services to prepare for Christmas. Please join us as we embrace the darkness and move into the light of Christmas.

Holiday Concert with the Vineyard Classic Brass Ensemble
5:30-6:30 pm, Chilmark library
Presenting their repertoire of holiday classics.

Thursday, Dec. 19
Men’s Night  5-9 pm, Rainy Day, Vineyard Haven
Sip, shop, and save for the holidays. 

Art Party: Upcycled Gnomes
6-7:30 pm, Oak Bluffs library
Make yourself a little holiday gnome friend using upcycled sweaters. 

Holiday Art Party
6-8 pm, Jazen’s Art Studio, Oak Bluffs
Create “Beach Ornaments” with Naomi. Listen to music and enjoy creating with friends. Bring your own drinks and snacks.

Handel’s Messiah
6 pm, Old Whaling Church, Edgartown
Grace Episcopal Church invites all to sing parts of Handel’s “The Messiah” along with soloists and guest conductors. A potluck reception will follow the event.

Friday, Dec. 20

Holiday Pop-Up
4-7 pm, Driftwood Jewelry, Oak Bluffs
Featuring Falk Designs and Island Venus Jewelry. 

Ugly Sweater Party
10 pm, the Cardboard Box, Oak Bluffs
Music by DJ AP. Midnight giveaway for the best/worst sweater. 

Saturday, Dec. 21

11th Annual Holiday Fair
10 am-4 pm, Grange Hall, West Tisbury.
You won’t want to miss this very special holiday fair, the last Vineyard Artisans Fair of the year.

Children’s Winter Tree Decorating
10-11:30 am, Oak Bluffs Library
Decorate an ice cream cone with frosting and festive toppings to create your own winter tree. Children under 8 must be accompanied by an adult.

Ukulele Jam: Holiday Favorites
1 pm, Oak Bluffs library
Join the Featherstone uke group as they play holiday favorites.

Holiday Cookie Swap Potluck
3 pm, Oak Bluffs library
Be prepared to come with four dozen cookies. Please bring a recipe card of ingredients to display.

Sunday, Dec. 22

Fourth Sunday of Advent
10:30-11:30 am, Federated Church Meetinghouse, Edgartown. Join us at Federated for the Advent Season. Sermon: “Hail Mary”, Rev. Richard S. DenUyl, Jr.

Holiday Hayrides
11 am-2 pm, Downtown Vineyard Haven
Enjoy a free holiday hayride in downtown Vineyard Haven, sponsored by the Vineyard Haven Business Association. Featuring Fred Fisher and sons.

Quiche and a Cause
12-3:30 pm, Vineyard Haven library
Learn about crafts and products produced by women’s empowerment projects around the world, just in time for last minute gift ideas.

Film: The Nutcracker
1 pm, Martha’s Vineyard Film Center, Vineyard Haven
This timeless holiday classic returns to the Bolshoi stage for a live broadcast.

Christmas Concert: An English Village Christmas
3 pm, First Congregational Church of West Tisbury
A concert of beautiful and haunting English Baroque works that express the mystery of the Christmas season, followed by folk carols and a hymn sing. 

Hanukkah Celebration
4 pm, Martha’s Vineyard Hebrew Center, Vineyard Haven
With Rabbi Caryn Broitman. Live music with Eric Johnson, Anthony Esposito, and Shirat Hayam. Sing Hanukkah songs, light your Menorahs, and eat Latkes. Please RSVP.

Monday, Dec. 23
Handel’s Messiah
2-4 pm, Vineyard Haven library
Singers of all ages gather to perform Handel’s Messiah.

Tuesday, Dec. 24

Christmas Eve Family Service
4 pm; St. Andrew’s Episcopal Church, Edgartown
With organ. All welcome.

Christmas Eve Candlelight Service
9-10 pm, Federated Church Meetinghouse, Edgartown
Bible readings, music by the Federated Church Choir, Peter R. Boak, Director. Service concludes with “Silent Night” and the lighting of candles

Christmas Eve Choral Service
9:45 pm; St. Andrew’s Episcopal Church, Edgartown
With organ and choir. Lovely and traditional. 

Christmas Eve Dinner
6 pm, Chappaquiddick Community Center
Festive dinner at the Chappy Community Center.

Wednesday, Dec. 25

Free Christmas Supper
1-5 pm, Oriental Martha’s Vineyard Lodge, Oak Bluffs
Oriental Martha’s Vineyard Lodge will host a free community supper on Christmas Day.

Christmas Dinner
5-9 pm, Bettini Restaurant, Edgartown
Four course prix-fixe menu. Enjoy wonderful family time around a table decorated for a delicious Christmas dinner. Reservations recommended.

Thursday, Dec. 26

White Elephant Gift Swap
1 pm, Edgartown library
Did you receive a gift this year that’s not quite “you”? Bring a new, in-the-package gift to this gift swap. Light refreshments served. All ages welcome.

Holiday Movies and Crafts
3-5 pm, Vineyard Haven library
Make crafts while watching movies.

Friday, Dec. 27
Holiday Movies and Crafts
3-5 pm, Vineyard Haven library
Make crafts while watching movies

Tuesday, Dec. 31

New Year’s Eve Celebration for Kids
10:30 am, Edgartown library
Enjoy refreshments, crafts, music, and a countdown to noon.

Holiday Movies and Crafts
3-5 pm, Vineyard Haven library
Make crafts while watching movies.

New Year’s Eve Prix Fixe Dinner
5:30-9 pm, Bettini Restaurant, Edgartown
Five-course chef inspired New Year’s menu with the option of including wine pairing with your dinner. Reservations recommended.

Roaring 20s Ball
9 pm-1 am, P.A. Club, Oak Bluffs
Dust off your flapper dresses or suspenders and wingtips and dance into 2020 with Joanne Cassidy and Mike Benjamin and their Big Band. Food, champagne toast, fire pit, and more. Cash prizes.

New Year’s Eve Party
10 pm, the Wharf, Edgartown
With music by DJ AP. Balloon drop and free champagne toast at midnight.

Wednesday, Jan. 1

First Day Brickyard Hike

10 am, Menemsha Hills, Chilmark
Celebrate the beginning of the year by hiking back in time. Access and trek the moraine off-public trails for this special morning hike to the storied brickwork ruins of the Trustees’ North Shore Property, Menemsha Hills. 

New Year’s Day Brunch
10 am-2 pm, Bettini Restaurant, Edgartown
Featuring assorted pastries, a made to order omelet station, oven baked Virginia ham, whole roasted roast beef, grilled salmon, baked mac and cheese, an array of sweet, sparkling flights, and build your own Bloody Mary’s.