A Winter Weekend in Martha’s Vineyard

As you may have seen on Instagram, recently I had the divine pleasure of traveling to enjoy Christmas in Edgartown. Every year I attend, it feels both familiar and novel as the island builds its itinerary and community. As a guest of the Martha’s Vineyard Chamber, I got to see all the wonders of this event.

However, what I really learned during my island moment is that you shouldn’t sleep on the Martha’s Vineyard off season. If you love comfort food, quiet walks admiring the frosty sand, and a cozy fireside – there’s something for you during the winter months on Martha’s Vineyard.

I have a whole post on why I love the off season here.

Many of the businesses and restaurants on Martha’s Vineyard close or reduce their hours after Christmas in Edgartown. However, in this post I’m going to highlight what is open during the winter months – so you know just what to do while planning to join the festivities next year.

Christmas in Edgartown

Where to stay

When going to Christmas in Edgartown, you have to be at the center of the action. The Harbor View Hotel is the perfect retreat, as this hotel overlooks the signature lighthouse. Watch from the porch with the coastal community as they light the lighthouse with a signature cocktail in hand. Continue your night by dining at the delectable Bettini (be sure to get their espresso martini) before heading a short few steps to bed. One of my favorite perks were the bikes AND the rental cars. With your stay, you are welcome to take one of the property’s Mercedes out for a 3 hour spin.

Pictures from my room overlooking the lighthouse can be found here.

In the off-season, I also suggest this hotel as the Harbor View reopens in late February. Which is cozy and open all year!

Shopping

Main Street open their doors for a Sip & Shop. The sales are just as crazy good as the homemade food at many of the stops. My favorites are Blackwater, KatyDid, the Black Dog and Nell (as Nell has a fortune cookie sale – crack one open and reveal a discount on their gorgeous, boutique clothing up to 60% off!).

Sight Seeing

Gay Lighthouse at Aquinnah Cliffs – check out the beautiful view from the cliffs without the summer crowds.

Menemsha is a small fishing village located in Chilmark. It has gorgeous see views, houses stilted over the water and a huge link to a very famous shark.

Edgartown Light – Walk down the path outside Harbor View Hotel to check out the Edgartown light in person.

To eat

Bettini – “Expansive windows reveal a magnificent coastal view that reinforces the kitchen’s relationship with the local landscape, creating a seamless island-to-table dining experience and the best of the island’s produce shines throughout the restaurant’s menus.” The food, ambiance and service was divine. You can’t go wrong with anything you choose off the menu. This is a Martha’s Vineyard vacation must.

Town –  a great bar open all year with a comforting menu with creative dishes and spins on classics including everything from pasta and seafood to steaks and bar bites.

Espresso Love – for your morning coffee and bagel craving.

Morning Glory Farm – a little bit of a drive, but a lovely option for baked goods and fresh produce if you booked an airbnb!

Christmas in Edgartown Events

Lighting of the Lighthouse. Walk up to the Harbor View hotel for a evening of fun for everyone. Enjoy gourmet cookies and a hot cocoa bar as you grab a photo with Santa Grab a drink at the Bettini bar at the Harbor View hotel and await the lighting of the lighthouse. Everyone gathers on the wraparound porch facing the sea as carolers sing your favorites into the wintery breeze.

Christmas in Edgartown Parade – Join the fun to see epic floats, animals dressed as reindeer, and of course Santa.

Vineyard Trust’s Holiday Cocktail Party at The Carnegie – Celebrate an Old-Fashioned Christmas with the Vineyard Trust. Enjoy fine cocktails and scrumptious passed hors D’oeuvres at  the beautifully decorated Carnegie

Murdick’s Fudge Hot cocoa – Don’t you dare miss the hot cocoa at Murdick’s Fudge. This delish concoction is only made once a year.

Wreath making at Donaroma’s nursery – Grab a souvenir and enjoy the festive display of lights at this greenhouse while making a festive wreath.

Sip & Shop: Main street, bop into the local shops. My favorites are Katydid, Backwater, Slate, and Nell.

Tips on Taking the Ferry

The Steamship Authority runs the ferry to and from Martha’s Vineyard. If you are taking a car, making a reservation with them is simply a must. They leave right out of Woods Hole and take you to Vineyard Haven, a 20 minute drive to Edgartown. While you can walk Edgartown, I always recommend bringing a car as the island is bigger than you think. However, there are Ubers and taxis on island if driving isn’t your thing. The Steamship Authority also offers overnight parking for passengers not looking to bring the car across.

Make a reservation. There is only one way across with your car. No matter the season, making sure you have a reservation is beneficial. If you don’t have one, you might be stuck in the standby line which is first come, first serve. During the summer or other peak events, you might wait hours to get across.

Check the weather. If there is a storm, ferries will not run. This is for safety reasons. It always pays to have a back up plan if you are stuck for another night. All weather advisories can be found by checking the website here.