When it comes to holly and jolly, the North Pole has nothing on this island of ours. On the second weekend of December, the holiday cheer-o-meter goes through the roof for the annual Christmas in Edgartown festival, with elves and snowmen parading down the streets and string lights aglow from Main Street to Edgartown Light. We know how easy it is to get turned around amid all the yuletide excitement — so make the most of it by taking a tip or two from some longtime festival-goers (that would be yours truly, of course).
Seasonal Sights To Keep From Slipping By
The weekend sees a lengthy lineup of holiday happenings from caroling to craft fairs, and as tempting as they all seem, you don’t want to schedule too much for yourself. Some of the seasonal sights we’d put in the “must-see” column include the Lighthouse Lighting on Friday night, the ever-exciting (and stupendously savory) Annual Great Chowder Contest, and the Arts & Crafts Festival, a gathering of over 30 island artists — a must if your holiday getaway includes the kiddos.
You also don’t want to miss your chance at a horse-drawn carriage ride — take it from us, the main ingredient to real holiday magic is casting a mesmerized gaze upon Edgartown’s light-strewn buildings and pine trees, backdropped by the rhythmic clopping of a stallion.
Greatest Angle To See The Lighthouse Light Up
On Martha’s Vineyard, we go way beyond decking the halls to kick off Christmas in Edgartown. Thousands gather to see our favorite seafaring structure, Edgartown Light, illuminate in bright reds and whites for our island version of a tree lighting. If you’re wondering which spot will grant you the greatest view, we recommend coming in from the beach trail right off North Water Street (it’s just a half-mile seaside stroll from our doors, so you can pass on the problematic parking situation). Head there early, around 3:00 p.m., to get a leg-up on the crowds — there’ll be plenty of cookies, hot chocolate, and holiday tunes to keep you warm and entertained.
Not feeling like joining the crowd for the up-close lighting experience? View it from a distance atop the Memorial Wharf on the waterfront — it’s a popular perch year-round, made even better when you can witness the lights switch on.
How to Feast on Festive Fare
For Christmas in Edgartown, it’s safe to assume that island restaurants will be bringing their A-game in both seasonal flavors and decor — so it’s also safe to assume that there will be some seat-savin’ competition. Always refer to the schedule of events to see if any area eateries are offering festive treats to eat on-the-go. Otherwise, we recommend setting your sights on a place to eat and putting your name on the list early on in the day. That way, you can partake in the festivities without a giant question mark hovering over dinner plans.
Hy-Line’s Santa-Approved Special Service
It’s no reindeer-led sleigh ride, but we’d place Hy-Line’s special service for Christmas in Edgartown a close second on the leaderboard of festive holiday transports. This service to Martha’s Vineyard was first rolled out in 2017 — in a rare off-season opportunity, you can cruise directly to Edgartown from Hyannis on any day of Christmas in Edgartown weekend.
Embracing The Holiday Spirit At Your Hotel
Before stuffing your stockings, stuff that suitcase full of holiday cheer during Christmas in Edgartown. The big weekend is just the beginning of a holly, jolly season around these parts — stick close to it all by making Vineyard Square your home for the almost-holidays. Not only will you keep close to all the holiday hustle and bustle, you’ll get to embrace the spirit with a crew as festive as you are (we’re a Scrooge-free zone).
These two favorite Martha’s Vineyard back roads link up nicely with the above routes for a day trip out to Aquinnah. When Edgartown Road ends in a T, turn left onto State Road, which becomes South Road. You’ll skirt along the shoreline near Lucy Vincent Beach—open to Chilmark residents only—before the road turns back inland. Now, in the center of Chilmark, turn left and take State Road southwest. Cross Stonewall Pond and thread the isthmus between Squibnocket Pond and Menemsha Pond before eventually ending up at the 
