2025 ISLAND HAPPENINGS BROUGHT TO YOU BY:
OAK BLUFFS
LIGHT UP OAK BLUFFS
11/29/25
The Oak Bluffs Association invites everyone to experience the magic of the season at Light Up Oak Bluffs — a festive day filled with family fun, local shopping, and community cheer. Circuit Avenue will sparkle with holiday lights, music, and merriment as we celebrate the start of the island’s holiday season.
Activities:
- Horse-drawn carriage rides from 1–3 PM
- 6 PM: Hot cocoa, candy canes, caroling, and reindeer antlers for kids in Healy Square
- 6:30 PM: The Grand Tree Lighting Ceremony in Healy Square
- Snowflake Scavenger Hunt
- Reindeer Games
- Shops featuring giveaways, treats, and specials for Small Business Saturday
- Christmas Open Market at The Strand featuring warm drinks, snacks, and Santa
This annual celebration brings together residents, visitors, and local businesses to ring in the holiday season with light, music, and community spirit.
WEST TISBURY
VINEYARD ARTISANS THANKSGIVING FESTIVAL
11/28/25 - 11/29/25
- Where: Grange Hall, 1067 State Road
- Dates: Friday, November 28, and Saturday, November 29, 2025, 10:00 am - 4:00 pm.
- Experience: The largest holiday art show and market by local artisans, featuring a variety of handmade holiday gifts, fine crafts, clothing, and artwork. Great food too!
VINEYARD HAVEN
Tis the Season
12/5/25 - 12/7/25
Friday, 12/5:
- Late Night Shopping - TBD
- Event at MV Museum- TBD
Saturday, 12/6:
- Regency Brass trio performs downtown - 12 - 2pm
- Santa’s Workshop at FISH - 12 - 2pm
- Fur Ever Memorial Tree
- Possible pop-up art market - TBD
- Tisbury Firetruck will join Santa’s Workshop - TBD
Sunday, 12/7:
- First Congregational Church of West Tisbury Bell Choir - 12 - 2pm
- Fred Fisher carriage rides - 12 - 2pm
Snow along Main St - Annual Shop-to-Share fundraiser: participating businesses contribute a percentage of all sales this day to Island Grown Initiative
- Possible pop-up art market - TBD
- Minnesingers & MVRHS Cookies - TBD
- Quartet Bell Choir outside The BeachHouse - 12 - 2pm
- Cape Cranberry Carollers - 12 - 2pm
- Fred Fisher carriage rides - 12 - 2pm
- Snow along Main St
EDGARTOWN
44TH ANNUAL CHRISTMAS IN EDGARTOWN
12/11/25-12/14/25
Now in its 44th year, Christmas in Edgartown remains one of New England’s most enchanting holiday celebrations. For four festive days — December 11–14, 2025 — our historic seaside village transforms into a winter wonderland filled with classic charm and island cheer.
Experience beloved traditions including the holiday parade, photos and visits with Santa, the magical lighting of the Edgartown Lighthouse, the bustling Holiday Faire, festive shopping events, live music, seasonal menus, charitable fundraisers, family activities, and over 100 special events throughout town.
Presented by the Edgartown Board of Trade, Christmas in Edgartown promises holiday magic for all ages — celebrating community, tradition, and the joy of the season in everyone’s favorite coastal escape.
Presented by
Photos by: Elizabeth Cecil for Visit Edgartown
Join the celebration — tag @VisitEdgartown
12/13/25 • 10am-3pm
Daniel Fisher House • Edgartown
Kick off the Holiday season with Handmade from the Heart!
All are welcome to come to support HPCMV at Handmade From The Heart on December 13th! Walk the streets of Edgartown and take in the spirit of the season. We guarantee you will find remarkable gifts for family and friends. Enjoy the beautifully decorated Dr. Daniel Fisher House, while eating treats at the Hospice-tality Café. Proceeds from treat sales go directly to our Christopher Fund. This fund has been helping patients and their families pay for out-of-pocket medical and related expenses since 1998.
PRESENTED BY
WITH SUPPORT BY
Don’t miss The Golden Ticket program kickoff!
The MV Chamber’s “Golden Ticket” program is an island-wide promotion designed to enhance the holiday shopping experience. Every $25 spent at participating local businesses earns shoppers ONE (1) Golden Ticket entry. Each ticket is a chance to win cash prizes in a grand drawing held on December 23 at The Black Dog in Vineyard Haven. *You do not have to be present to win!*
- Hotels: 1 golden ticket for $100
- Restaurants: 1 golden ticket for every $25 spent on the bill
GOLD RUSH:
As part of this program, there will be three (3) GOLD RUSH events to generate even more excitement. These events will take place on Small Business Saturday, November 29, Vineyard Haven Celebration, December 6 and Christmas in Edgartown weekend, December 11-14. During these special days, participating businesses will distribute two (2) tickets for every $25 spent, boosting sales and adding to the festive fun!
The participating businesses are listed below and will display a decal in their window, letting you know they’re part of the Golden Ticket Program!
Honor the memory of a beloved pet this holiday season.
The tree will be hosted at The Black Dog Campus, 20 Beach Street Extension, Vineyard Haven, as we kick off our Tree Lighting on
Saturday, December 6, 2025.
How to Participate
Deadline for inclusion in the lighting: December 5
Drop off:
Bring a photo and your pet’s name to the Chamber with $10 (cash or check):
24 Beach Street, Vineyard Haven
Mail:
Send your photo and pet’s name to:
MV Chamber of Commerce
PO Box 1568
Vineyard Haven, MA 02568
Contribution:
Please include $10 (cash or check). Your photo will be laminated and hung on the tree.
Thank you for helping us celebrate the pets who filled our lives with love while supporting local animal welfare.
A portion of proceeds benefits the MV Animal Shelter.
2025 GOLDEN TICKET PROGRAM PARTICIPANTS:
- 51 Art Gallery
- Aligned Pilates
- Austin Designs
- Black Dog General Store
- Bryn Walker
- Coastal Supply Co.
- Conrado
- Erica Wilson
- Island Alpaca
- Island Time
- Jardin Mahoney
- John Keene Excavation
- KIN
- Lani Beach Club
- Morrice Florist
- Newes From America
- Offshore Ale
- Olive Branch Fair Trade
- Oso
- Our Market
- Rainy Day
- Sea Spa
- Stefanie Wolf
- Stop & Shop
- Summer Shades
- Taylor Stone Illustration
- Tending Joy Artisan Shop
- The Green Room
- The Maker
- Yoga On the Vine
- Your Market