Enjoying Edgartown in the Off Season

by Cheryl Hackett
Home & Historical Editor


From Maine to Connecticut, New Englanders know how to savor changing seasons and the endless variety of vacation spots. In the spring, we flock to Boston to enjoy the marathon, baseball and swan boats. In the summer, we head to Cape Cod and the Rhode Island shoreline to bask on beaches. In the fall, we marvel at foliage in the Berkshire’s foothills. And in the winter, the Green Mountains and White Mountains beckon us with snow covered slopes.

When we need a weekend getaway, these are our traditional migratory paths. However, some of us are known to tempt fate by exploring popular destinations in the off-season. It’s not that we’re introverts trying to avoid crowds. Instead we simply appreciate stillness. When distractions are few, we can truly experience the region’s spectacular scenery, rich history, storied architecture, and hearty cuisines.

“Live each season as it passes; breathe the air, drink the drink, taste the fruit, and resign yourself to the

influences of each.” - Henry David Thoreau

I recently had the opportunity to visit Edgartown, one of the six towns on the island of Martha’s Vineyard. During the height of the summer tourist season, the Vineyard’s population swells beyond 100,000 people. After Labor Day, the population drops to 17,000 year-round residents. September to May are ideal times to enjoy the island and all her charms. The 45-minute Steamship Authority ferry ride from Woods Hole to Oak Bluffs was effortless. No ticket lines, no snack bar lines, and plenty of window seats to choose from. A fleet of taxi drivers were waiting at the ferry landing and the ten-minute $23 ride to the Kelley House in Edgartown included an impromptu tour and a restaurant recommendation from a gregarious driver. Serendipitously, the driver gave his highest rating to the Newes from America Pub located at the Kelley House.

Soon after checking into a well-appointed room overlooking the waterway between Edgartown and Chappaquiddick, I met with Elizabeth Rothwell, Regional Director of Marketing for Scout Hotels. Scout Hotels also operate the Harbor View Hotel in Edgartown, which happens to serve a spectacular breakfast in a dining room that overlooks the Edgartown Lighthouse. The iconic structure ranks among local artists’ favorite scene to paint.

Martha's Vineyard description

Edgartown Light House on Martha’s Vineyard

Elizabeth described the Kelley House by saying, “A fixture on the Vineyard for over 250 years, Kelley House is known for its hospitality, welcoming atmosphere and charming location. Set in the heart of Edgartown, it’s the perfect starting point for our guests to discover the Vineyard’s charm. While a year-round destination, the off-season is my personal favorite. Offering a cozy fall and winter respite without summer’s crowds, Kelley House appeals to visitors looking to enjoy life’s simple pleasures.”

She added, “I recommend taking one of our custom bikes for a spin around town. A tour of our brand new Kelley House Gallery followed by a bite to eat at our Newes From America Pub will make for the perfect Edgartown afternoon.”

The weather was picture perfect during our island respite; the sun was shining brightly, and the weather app on my I Phone reported a balmy 62 degrees. My architect-companion joined me on a peaceful stroll through the lovely neighborhoods distinguished by 18th and 19th century sea captains’ manses. From North Water Street to Pease Point’s Way to School Street, we were charmed by a myriad of exquisitely preserved homes with white clapboards, dark green shutters, white picket fences, and gardens still blooming with late summer divas such as roses and hydrangeas. Many of the homes were closed for the season and their serene inactivity made them all the more poetic.

When we returned to the Kelley House we enjoyed their new art gallery in the lobby that features large monitors that display a seemingly endless exhibit of photographs that capture the Vineyard’s extraordinary beauty. Perhaps it is not a coincidence that the most stunning and poignant images were photographed during the off-season.

Next on our itinerary was dinner at the Newes From America Pub. When we entered the cozy historic setting, were greeting by the sweet sounds of folk music being performed by a local dual. The tables were filled with a combination of local families and other couples enjoying the pub fare. Feeling adventurous, we ordered the seafood stew that featured shrimp, scallops, and lobster in a rich creamy Newburg sauce. The pieces of lobster were so large that we alternated between using forks and spoons to enjoy every delectable bite.
On the second day of our trip, we visited the many high-end boutiques that line Main Street. An off-season perk was proudly displayed in every window……End of Season Sales Signs. Discovering a beautiful cashmere sweater priced at a 75% discount was cause enough for a happy dance.

While visiting the shops, I kept asking the shopkeepers what was the best aspect of the off-season in Edgartown. The common refrain was a resounding Christmas in Edgartown . The 34th annual event will take place this year from December 10 – 13. The event features special sales in the boutiques, food tasting events, caroling, and a parade with Santa Claus. Santa’s final destination is the Kelley House lobby, where the jolly old soul sits by the fireplace and poses for pictures with children and the young at heart. Most everyone I spoke to about the event mentioned that now is the best time to book a room because the hotels sell out quickly for the event that is guaranteed to put you in the holiday spirit.

Nancy Gardella, Executive Director of Martha’s Vineyard Chamber of Commerce  says, “Christmas in Edgartown isn’t just a wonderful weekend of holiday fun – it captures all the iconic elements that makes the Vineyard so special: amazing local food, arts and culture, one-of-a-kind shopping and a cozy sense of community in the backdrop of natural beauty.”

So if you are looking for some rest and relaxation and a jump on your holiday shopping, why not consider staying in Edgartown?


Christmas Happenings in Edgartown

Weekend of December 11th – 13th

Annual Lighting of the Lighthouse

Martha's Vineyard description

Don’t miss the Annual Lighting of the Lighthouse! Enjoy hot chocolate, holiday goodies, music on the hotel porch and more. Enjoy the holiday cheer as everyone counts down to the much anticipated lighting of the light Lighthouse. Please call Betsey Mayhew at 508-627-4441 x 112 for more information.

Sponsored by MV Museum & Harbor View Hotel

December 11th

5 pm to 7 pm

location:  Harbor View Hotel

Check out what else is happening below and more fun happening  here including the Annual Christmas Parade!


Local Arts & Crafts Fair 


Take care of your holiday shopping while supporting local artisans and enjoying a pint from the Newes Pub.

Dec. 11th | 5 pm-8pm

Dec. 12th | 9 am – 5 pm

Dec. 13th | 9 am – 1 pm

Chappy Room at the Kelley House




Beer & Cheer

at Bad Martha Brewery

Bad Martha

Brewery tours and beer tastings ! This is a great chance to shop gifts for the craft beer lover in your life and enjoy a pint of your favorite brew.

Dec.  11 -13
2:00 PM – 9:00 PM

Bad Martha Farmer’s Brewery

 Josh – 508-939-4415





Minnesingers Concert

 The Old Whaling Church


The MV Preservation Trust presents the Island’s premier high school choral group, the MVRHS Minnesingers, to perform a concert of seasonal favorites at the magnificent Old Whaling Church.

Dec. 11th
8:00 PM – 8:00 PM

Old Whaling Church

Janet – 508-627-4440

Tickets are $15.00 per person.

Cocktail Party

at Dr. Daniel Fisher House


Celebrate and old fashioned Christmas at the Beautifully decorated Dr. Daniel Fisher House with the MV Preservation Trust. Enjoy holiday cocktails and passed hors d’oeuvres by Buckley’s Gourmet Catering.

Dec. 11th
5:30 PM – 7:30 PM

Dr. Daniel Fisher House

Janet- 508-627-4440

Tickets are $65.00 per person.


Christmas Tree Art Display



Come view beautiful Christmas trees decorated by local art groups from throughout the island. The trees will be on display and lit all weekend long. Sponsored by the Edgartown Board of Trade and The Boathouse.

Dec. 11 – 13
12:00 AM – 12:00 AM

Atlantic Fish & Chophouse



 Wreath Making

at Donaroma’s Nursery



Call and sign up for an annual favorite! Join Donaroma’s for their workshop on how to create your own beautiful boxwood tree, wet or dry wreath. This event is a Christmas in Edgartown favorite so call in advance to secure you space.

Dec. 12th
10:00 AM – 4:00 PM

Donaroma’s Nursery

Sue – 508-627-8366 for reservations

$30 – $40 per person.

The Kelly House kindly hosted Cheryl Hackett for her stay in Martha’s Vineyard. Her opinions expressed are her own.

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