Make it a Very Vineyard Holiday! Explore the charm of Martha’s Vineyard this December by visiting the three “Down-Island” towns—Edgartown, Oak Bluffs, and Vineyard Haven. Each offers unique holiday experiences, from dazzling light displays to cozy holiday markets. Here’s your guide to The Most Enchanting Places on Martha’s Vineyard to Visit This Holiday Season
The Most Enchanting Places on Martha’s Vineyard to Visit This Holiday Season – Edgartown: A Classic New England Holiday Scene
Edgartown transforms into a winter wonderland during the holiday season. Its cobblestone streets, historic homes, and harbor views set the perfect backdrop for festive events.
The Lobster Pot Tree
A true Vineyard tradition, the Lobster Pot Tree in Edgartown is a quirky and beloved landmark. Constructed entirely of lobster pots and adorned with twinkling lights, this unique tree celebrates the Island’s maritime heritage. Take a stroll down Main Street to see it, and don’t miss snapping a photo of this iconic display!
The Teddy Bear Suite
Founded and sponsored by Point B Realty, the Martha’s Vineyard Teddy Bear Suite is an annual holiday fundraiser that brings magic and joy to the season while supporting a meaningful cause. Now going into its 14th enchanting year, the Teddy Bear Suite has become a beloved tradition for families visiting Edgartown during the holidays, coinciding with the Christmas in Edgartown weekend. The suite this year will be located at both 19 and 29 Winter Street, in Nevin Square.
Each year, this whimsical experience comes to life with beautifully decorated spaces and a delightful collection of holiday-themed teddy bears, creating a cozy and festive atmosphere. Proceeds from the event benefit the Martha’s Vineyard Boys & Girls Club’s After School Programs, making it a wonderful way to spread cheer and give back to the community. In our first 13 years, we raised $425,000.
The Carnegie
Step into Edgartown’s historic Carnegie building for a dose of holiday spirit thanks to the Vineyard Preservation Trust. This cultural hub often features special seasonal exhibits, gift ideas, and opportunities to learn more about the town’s storied past. From November 30th through December 21st you can enjoy the magical Dickens Christmas Village, a collection of intricate miniatures, model trains, and enchanting scenes that bring Victorian holiday traditions to life.
The Historic Vincent House, Built in 1672
Enjoy the festive spirit and charm of Christmas past in the Island’s oldest house located at 99 Main Street in Edgartown and maintained by the Vineyard Preservation Trust. Expert guides share captivating stories of the Vineyard’s early rural Christmas celebrations. Dates include: Saturdays, Nov. 30,12–2pm; Dec. 7,12–2pm, Dec. 14,12–4pm, and Dec. 21, 12–2 pm.
Stroll Through Town
Take a leisurely stroll through Edgartown’s beautifully lit streets to soak in the holiday atmosphere. Enjoy the charming window displays, historic homes adorned with twinkling lights, and festive shopfronts. The views of Chappaquiddick and the harbor from Memorial Wharf are especially enchanting this time of year. If you’re visiting during the Christmas in Edgartown weekend from Dec 12-15th, you’re in for a treat! The town comes alive with holiday spirit, offering seasonal menus in restaurants and special pop-up shops filled with unique gifts and festive cheer.
Donaroma’s Holiday Wonderland
This beloved garden center goes all out for the holidays, creating enchanting displays of lights, ornaments, and seasonal plants. Whether you’re looking for unique gifts, wreaths, or just some holiday inspiration, Donaroma’s is a must-visit spot for holiday cheer.
The Most Enchanting Places on Martha’s Vineyard to Visit This Holiday Season – Oak Bluffs: A Festive and Fun Wonderland
Ocean Park
Ocean Park is the heart of the holiday festivities in Oak Bluffs. During the Light Up Oak Bluffs celebration, this picturesque park becomes a beacon of holiday cheer. The iconic gazebo and surrounding trees glow with festive lights, creating a magical atmosphere. On November 30th, enjoy reindeer games on the lawn, live holiday music, horse-drawn carriage rides and the grand finale—the annual tree lighting ceremony at 6:30 om in Healey Square. Santa himself makes a special appearance, arriving on a fire truck to the delight of all.
Festive Events Throughout Town
Oak Bluffs brims with holiday activities throughout the season. On November 30th, immerse yourself in the spirit with Light Up Oak Bluffs, a day long event which includes a Snowflake Scavenger Hunt at Stefanie Wolf Designs and an opportunity to pose for photos with Santa and his elves in Healey Square. For a touch of nostalgia, hop on a horse-drawn carriage ride by Sonnyside Rides, departing from Eastaway, or snap a festive picture in front of the Vineyard Gazette truck at the Morgan Hotel. As the day winds down, warm up with dinner at local favorites like Offshore Ale Co., Pawnee House, or Linda Jean’s.
Featherstone’s 22nd Annual Holiday Gift Show
Featherstone Center for the Arts hosts its highly anticipated Holiday Gift Show from November 12th to December 15th, featuring handmade gifts from local artists. From pottery and jewelry to paintings and photography, this is the perfect place to find one-of-a-kind treasures while supporting Island creatives. The show is open daily from 12–4 PM, with the exception of Thanksgiving Day.
The Gatchell House Light Display
A visit to the Gatchell House on County Road is a must during the holidays. Renowned for its extravagant decorations, this festive privately owned home is adorned with glowing reindeer, animated figures, and over 20,000 twinkling lights that captivate visitors of all ages. It’s a spectacular spot to soak in the season’s magic and take in the creativity of one of Oak Bluffs’ most beloved traditions, which has been happening for over 40 years. Visitors are encouraged to bring nonperishable food items or a monetary donation for the Island Food Pantry. The display typically kicks off the Friday after Thanksgiving.
The Most Enchanting Places on Martha’s Vineyard to Visit This Holiday Season – Vineyard Haven: Cozy Markets and Artistic Delights
The year round port town of Vineyard Haven is filled with classic New England holiday charm, offering a mix of history, community events, and festive shopping opportunities. With its lively Main Street, iconic Black Dog campus, and rich cultural offerings, Vineyard Haven invites you to embrace the season in style.
Martha’s Vineyard Museum
The Martha’s Vineyard Museum becomes a festive centerpiece during the holidays, hosting seasonal events that blend history and holiday cheer. On Friday, December 6th, enjoy the Museum’s First Friday event from 4:30–6:30 pm, featuring special exhibits and live music. That evening, music will fill Main Street from 6–9 pm, adding a magical soundtrack to the evening’s stroll. On Saturday, December 7th, the Museum’s Holiday Soirée from 5–7 pm offers an elegant way to celebrate with seasonal decor, refreshments, and entertainment.
The Black Dog Campus Celebration
A visit to the Black Dog campus during the holidays is a must. On Saturday, December 7th, the campus comes alive with festive activities from 2–5 pm, including photos with Santa, culminating in a heartwarming Giving Tree Llighting ceremony in collaboration with the Martha’s Vineyard Chamber of Commerce at 5 pm. Stroll through this iconic Vineyard destination, enjoy holiday treats, and find unique gifts for the season.
Strolling Main Street
Main Street in Vineyard Haven is the perfect place to soak in the holiday spirit. The shops extend their hours for late-night shopping on Fridays (December 6th, 13th, and 20th) from 5–8 PM, offering a chance to find the perfect gift while enjoying the festive atmosphere. On Sunday, December 8th, Main Street will be alive with traveling carolers, a bell choir, and carriage rides that evoke a sense of holiday nostalgia. The day also includes the Artist Market on Union Street from 10 am–2 pm and the “Shop to Share” initiative, where participating businesses donate 10% of proceeds to Island Grown Initiative.
Winter Wonderland Activities
On Sundays, December 8th and 22nd, Vineyard Haven will host a Winter Wonderland experience featuring Santa’s Workshop at Waterside Market and more seasonal delights. These family-friendly events make for a magical holiday outing.
Making the Most of Your Holiday Visit
Plan your itinerary to explore all three towns and experience the best of what the Vineyard offers this holiday season. Whether you’re browsing local markets for unique gifts, admiring stunning light displays, or soaking in the seasonal charm, there’s something magical to discover at every turn. Don’t forget to bundle up—it’s the perfect time of year to enjoy a warm drink from a local café while exploring the Island’s festive streets. For a comprehensive list of holiday events happening across the island keep checking the MVY Chamber’s Very Vineyard Holiday webpage to stay in the know.