By Cynthia Roderick

For the last two years, my sisters and I have met on Martha’s Vineyard to celebrate the winter holidays at the Christmas in Edgartown festival. The weekend event is usually held in early to mid-December.

For three days we feast and laugh and sing. We ooooh and ahhh at the holiday lights and candles displayed at Donaroma’s Nursery, a must stop for everyone.

There, we sing carols and listen to the bell ringers and stand around a huge bonfire and feel so lucky to be part of this island celebration.

Inn to Inn

We amble arm-in-arm from one quaint and beautiful inn to another on the event’s lauded Inn Tour. And we shop at the close-out sales offered by the town’s upscale stores, emptying inventory before their winter vacation.

When on Sunday we board the ferry — I prefer the Island Home, the newest boat — we are wrapped in the conviviality and richness of our time together.

We leave our cars on the freight deck, and go upstairs for tea or coffee and to read our newspapers. Then we settle quietly into the cushioned seats and enjoy the waves and gulls on the 35-minute trip back to Woods Hole on the mainland.

“We all think of holiday time as hectic,” says Nancy Gardella, executive vice president of the Martha’s Vineyard Chamber of Commerce. “This is a chance to give yourself a weekend break and experience something unique. There are no billboards, no fast food, no Walmart. We offer a one-of-a-kind experience with traditional New England holiday fare. But here Santa comes by boat.”

The Christmas in Edgartown celebration is scheduled for mid-December.

Tour of the Inns

When my sisters and I arrive around noon on Friday, we unpack and get ready for the free tour of the historic Inns. For many visitors, this is the highlight of the weekend.

The tours are on Friday and Saturday from 2 to 4 pm. I’m so glad I brought my camera, and you will be, too! You’ll want to show your friends these 19th-century mansions with their white picket fences built during Edgartown’s whaling heyday.

You can wander from one inn to another — this year three of them are located within houses of each other — and look at the beautifully appointed guest rooms. Some are so special, they’ll truly leave your senses sated.

If they don’t, the owners will have laid out a spread of holiday desserts and drinks for you — an array of cookies, fudge, brownies, date squares, holiday fruit breads, and more and everything to drink from egg nog made with real whipped cream to various punches, ciders, coffee, and tea.

Make Merry at the Inns

While you indulge and make merry, you can take a leisurely break in the dining rooms or make yourselves comfortable on the many sofas in common rooms on the main floors.

And if you’re lucky as I was last year, Santa Claus or a group of carolers in homemade Dickens-era costume will stop by to entertain you.

Four inns will participate in the tour: Shiverick Inn, Hob Knob Inn, Ashley Inn, and Kelley House, which is a short walking distance from the others.

While you’ll likely want to visit all of the inns, my favorite was the Charlotte Inn, which was on the tour last year, and perhaps you could stop by this year anyway.

The Charlotte Inn, built for Samuel Osborne, a wealthy merchant, in 1864, is wall-to-wall antiques. The lavish, Edwardian-style furnishings create a densely atmospheric space — not a bare spot to be found either on the walls or along them. I never tired of walking from one room to the next, and the hallways are just as interesting.

Conde Nast Traveler awarded the inn a Reader’s Choice Award. It is also listed among the Top 100 Best-in-the-World Properties.

The Shiverick is another elegant inn reflecting the grandeur of a bygone era. Built in 1840 for the town doctor, today the recently restored inn features a distinctive ambience in each room, suite, and common room—all furnished in opulent fabrics, antiques, wallpapers, and oriental rugs.

The Christmas in Edgartown celebration is “the kick-off for Christmas,” says Dr. Paul Weiss, one of the inn’s owners. “Stores open this weekend with big sales, and Santa arrives in town.” The inn is a favorite for festival-goers.

The Shiverick really won my heart when I learned that several rooms are available to guests with their best friends in tow: I mean their dogs, of course. This added feature can be helpful for anyone participating in the parade on Saturday, during which residents and visitors get to show off their favorite pets.

The 10-room Victorian-style inn boasts seven welcoming fireplaces, with two in the common areas.

The Hob Knob is a 19th-century mansion with 17 rooms — including 11 king size beds — and two private guesthouses.

John F. Kennedy stayed in one of the rooms while visiting Edgartown for a sailing regatta in 1947, the summer after he first took a seat in the US Senate. The Hob Knob, a welcoming place as you might guess by its name, is appreciated by guests in part for its eco-friendly ways including non-toxic cleaning materials.

The Ashley Inn was built in 1860 by a retired sea captain. His descendants lived there until 1983 when it was turned into a charming Bed and Breakfast. It’s 10 rooms display beach and sea themes in soft pastels making you expect a soft summer breeze. The recently renovated common room sitting area has a number of comfortable couches and an inviting feeling.

Founded in 1742, the Kelley House Hotel has been known by many names in its various iterations and today is among the Historic Hotels of America.

The hotel, located in the center of town, boasts a number of suites with balconies overlooking Edgartown Harbor and its many yachts. The rooms are spacious and modern but not available during the winter season.

The hotel and its pub, Newes from America, provided sustenance to Hollywood types in the early 1970s when the making of Steven Spielberg’s Jaws on the Vineyard stretched from five weeks to five months.

This is a stop especially for those interested in maritime artifacts… and perhaps a glass of red wine. The fare at the restaurant served year-round, is tasty and affordable.

Dinner, then Over to See the Lights

In the evening we have dinner at one of Edgartown’s fine restaurants, the Square Rigger–the fresh fish and baked, stuffed lobster ($33) alone are worth the trip, but don’t miss the ample prime rib ($32), either.

Then we walk across the street to Donaroma’s to see the sparkling lights and sing. People from the community participate in the festivities here: the bell ringers, the carolers, angelic looking children in halos and wings. Everybody is excited by the holiday spirit.

On the grounds, you can find bonfires, all sorts of trees and bushes and animals figures adorned in colorful lights.

Donaroma’s greenhouses are alive with the warmth of candles, the aroma of pine cones and evergreens, and the sparkle of crystal bowls and candleholders.

If you need ideas for table arrangements, this is a good place to stock up. Lights twinkle across the ceilings amidst wisps of white that resemble snow. Punch, warm apple cider, and cookies are served, all for free.

On Saturday, you can participate in the wreath-making workshop from 10-4. Sign up by calling 508-627-8366. Visit the website at: donaromas.com.

The Parade, Shopping

The parade begins on Saturday at 10 am. Expect to see reindeer — actually, ponies with felt racks. There are dogs of many breeds, some dressed festively and happily dragging their owners by a leash, except when they stop to sniff one another—the dogs, that is.

Red-cheeked children line the sidewalks licking candy canes, or they ride by on floats tossing hard candies to onlookers.

After the parade my sisters and I split up, some of us to visit the town’s numerous art galleries: Carlin Fine Art, The Christina Gallery, Edgartown Art Gallery, Eisenhauer Galleries, Gardner Colby Gallery, and Willoughby’s.

Some of us prefer to shop. I especially love the Hospice of Martha’s Vineyard fundraiser. Called “Handmade by the Heart,” it’s held at the Daniel Fisher House on Main Street.

Island women have knitted and sewn lovely scarves, sweaters, and blankets; hats, mittens, and more. You can buy them at amazing bargain prices: $20 for a colorful child’s sweater!!

At the same time, you will be fostering the continuation of an important service. Get there early, as people in-the-know go there first for their holiday shopping.

Chowder Time

At noon, it’s time for the Annual Great Chowder Contest. Last year, the admission was $5.00 and well worth the price. The event is held on Main Street under a large white tent.

Indulging in cup after cup of the most interesting fish and clam chowders and soups will get you thinking about tastes in a new way. You can vote for the best, which often necessitates a second round of your favorites, essential to making a considered decision.

Winning is taken very seriously, but not too seriously, as all are quite delicious. Last year, the Harbor View Hotel came in first, and I felt gratified that my taste buds had agreed with island connoisseurs.

Family Concert

At 4 pm, the Minnesingers Holiday Family Concert is held in the Old Whaling Church, a beautiful, spare building with towering Greek columns. Inside, students from the Martha’s Vineyard Regional High School fill the large, empty space with truly thrilling sound. They sing everything from classical songs to popular carols to gospel songs with equal enthusiasm and skill.

My spirits truly lifted, I left the performance wondering how a collection of high school students on this small island could produce such exquisite sound. The concert is $10 for those 13 and over.

If you still have the energy, you can attend the lighting of the town Christmas tree on the Village Green. I’ve always wanted to go. Instead, I find myself curled up in a comfortable chair sipping wine by the fireside and chatting with the beautiful women in my family and relishing this family tradition.

Sunday, and Home

On Sunday, there’s a Christmas Breakfast with Santa from 8 to 12:30 at the Wharf Restaurant. And at 10:30 families can join the Treasure Hunt for Kids.

Alas, by Sunday morning I’m ready for hot coffee and subdued conversation and preparations for the trip home.

The Board of Trade has a complete schedule of the holiday events online at: edgartownboardoftrade.com

Remember, there are a number of smaller events not listed there, so ask around, explore, and you will find lots of fun and family fare.

Getting There

The Steamship Authority is the only company that takes both passengers and cars and trucks. The boats leave from Woods Hole and land in Vineyard Haven or Oak Bluffs. I prefer to land at Vineyard Haven. Adults, $15 RT; children 5-12, $8 RT. Cars from $135-$155, depending on length.

If you decide to leave your car in one of the Steamship Authority’s parking lots, there are taxis to take you to your lodging. You won’t need a car during the Christmas in Edgartown festival, but if you have your car with you, you can tour the rest of the island or visit the other towns.

Where to Stay

The Vineyard Chamber of Commerce website list places to stay.

Tel: (508) 693-0085 or toll free (800) 505-4815.

Here’s a varied selection:

Shiverick Inn
5 Pease’s Point Way
Edgartown, MA 02539
(508) 627-3797
10 rooms starting at $130 nightly

Hob Knob Inn
128 Main St
Edgartown, MA 02539
(508) 627-9510
20 rooms starting at $175 nightly

Ashley Inn, a Bed and Breakfast
129 Main St
Edgartown, MA 02539
(508) 627-9655
10 rooms starting at $115 nightly

The Charlotte Inn
27 South Summer St.,
Edgartown, MA 02539
508-627-4151
23 rooms, $295-$695 nightly
2 apartments, $550-$950 nightly

The Arbor Inn, a Bed & Breakfast
222 Upper Main St, Box 1228
Edgartown, MA 02539
Phone: 508-627-8137
Toll Free: 888-748-4383
9 rooms, $115 – $250 nightly

The Farmhouse Bed & Breakfast
State RD
West Tisbury, MA 02575
Phone: 508-693-5354
5 rooms, $75 – $150 nightly

Kelley House, located at 23 Kelly St., though on the tour is not open to guests in winter.

Where to Eat

The lists restaurants open in winter.

I recommend the following:

Détente Restaurant and Wine Bar
Winter St, Nevins Square
Edgartown, MA 02539
508-627-8810
American, Contemporary, $25-$40

Water Street Restaurant
131 N Water St
Edgartown, MA 02539
Phone: 508-627-3761
Serving year-round; Breakfast, Brunch, Lunch, Dinner, $8 – $48
American, Seafood, Continental, Contemporary

Square Rigger
Upper Main St
Edgartown, MA 02539
Phone: 508-627-9968
Open for Dinner Year-Round
American, Seafood

Cynthia Roderick is a photographer and writer living in South Deerfield, Massachusetts. Visit her website, cynthiaroderick.com.