When it comes to Christmas trees, Oak Bluffs landscaper Mark Crossland might be the Martha’s Vineyard champion of good cheer. Each year he and his employees decorate Ocean Park with dozens of “light trees” formed with a center pole, ropes and about a gazillion LED lights. All the light trees are anchored by a beautifully decorated real tree in the Ocean Park Bandstand.

“We just kind of position them around the park so it looks like a little village,” said Mr. Crossland. “Every year I add to it. This year we added 31 more trees.”

Another new twist added this year is holiday music, which is synchronized to some of the light trees.

“It’s really cool,” he said. “It’s a light controller. You program an SD (memory) card with music that you want. Certain beats, the amber trees will go off, the aqua trees will go off on different beats. The drums make the green trees light.”

The music plays from the bandstand on Friday, Saturday and Sunday evenings, and it is also broadcast on a low power radio frequency at 88.5 FM, so tree watchers can sit in their cars to enjoy the show.

Placing a tree on Sunset Lake is Mark Crossland's favorite holiday puzzle. — Steve Myrick

As much as he likes the Ocean Park display, Mr. Crossland’s favorite tree is the live decorated tree that floats on Sunset Lake near the Oak Bluffs Harbor.

“I have a raft. We set it up on the shore, decorate it, get everything set so we can’t blow fuses,” said Mr. Crossland. “Then we take a kayak and row it out there.”

Mr. Crossland won’t say how he gets the electricity out to the tree, so it will have to remain a trade secret for now. In any case, it’s a complicated operation, especially if there is wind or current in the lake.

“We have a line to the shore to get it positioned right,” said Mr. Crossland. “We get it in the right location and we anchor it. We’ve done it for about 10 years, so it gets easier and easier.”

Close observers of Vineyard Haven Harbor look forward to the day each Christmas season when small evergreen trees are hoisted to the mastheads of the Black Dog schooners Shenandoah and Alabama.

“We’ve been doing it on the tall ships for as long as I can remember,” said Rob Douglas Jr.

Captain Robert Douglas said he doesn’t know the origins of the tradition, but he has an inkling it may have started with Norse seamen ages ago. It may also be adapted for the holidays from the European custom of “topping off,” or placing evergreens at the masthead when the final mast of a wooden ship is set, to honor or appease the forest spirits where the wood was harvested.

Captain Douglas said he has seen pictures of only one other schooner with Christmas trees on the mastheads, and that was a cargo schooner that plied the Great Lakes each season with loads of Christmas trees in her holds.

“I don’t think I’ve ever seen any other pictures of boats with Christmas trees at their mastheads,” Captain Douglas said. “We’re just carrying on tradition as I know it.”

Dr. Daniel Fisher House in Edgartown is aglow for the holidays. — Steve Myrick

Funi Burdick, executive director and CEO of the Martha’s Vineyard Preservation Trust, feels the holidays are a time of community. She says nothing illustrates that better than when board members Carole Berger and Theadora (Teddy) Ellis lead a merry band of volunteers in decorating Christmas trees at the Dr. Daniel Fisher House in Edgartown.

“The Christmas tree represents a community spirit,” said Ms. Burdick. “When you have people coming together, to decorate trees together, you start to feel like the Island is one big family.”

The Preservation Trust’s chief Christmas tree putter-upper is Robert Ribeiro. It takes him about two weeks. Counting the carefully pruned and coincidentally shaped shrubbery on the grounds, there are 11 decorated trees at the Fischer House.

“A lot of trees, he said. “A lot of trees.”

The whole process starts before Thanksgiving, with the selection of the Christmas trees, a job he takes very seriously.

“I was the first one to pick up the tree at Donaroma’s,” said Mr. Ribeiro. “Nobody else had picked up their trees yet, so I could find a really good one. It’s full, there’s no holes, no empty spots. I like to be there first and pick a really good one.”

Mr. Ribeiro was a math teacher in his native Brazil, and his affinity for order and logic is evident in the precise spacing of the lights on the outdoor trees.

“I do zigzags, try to space them equally, although the wind is messing up my work,” he said with a laugh.

At the Donaroma’s annex on State Road in Vineyard Haven trees of every size and description lean against wooden stands. There are two-foot tall table top balsams all the way to 10-foot tall Frasier fir giants. Manager Belinda Booker says she has lots of happy customers, even before they arrive at the shop, and they come throughout the holiday season, starting even before Thanksgiving.

“They love Christmas trees, who doesn’t,” Ms. Booker said. “We definitely do have early birds.”

Donaroma's annex in Vineyard Haven is greenery central. — Steve Myrick

Others are Christmas Eve tree trimmers.

“Some people come in three days before Christmas,” said Ms. Booker. “They have a family tradition.”

It is her favorite time of year, she said, the best part of her job. Sometimes it takes a little shopping to find the perfect, beautiful tree.

“It’s all in the eye of the beholder,” said Ms. Booker. “I personally like a skinnier kind of tree. I like to place my ornaments inside the tree, put the lights all inside the tree. Others like the big fat trees.”

Down the road a bit, tree buyers can get a bit of charity with their good cheer at the Legion Pumper Christmas tree operation. For as long as anyone can remember the Tisbury fire department has sold Christmas trees on a small lot next to Hinckley’s Lumber.

“It’s a tradition that has gone on for generations,” said Tisbury fire chief John Schilling, who took many a volunteer shift selling trees when he was a member of the Legion Pumper company (since the middle of the last century, Engine 3 in the Tisbury fire department has been known as the Legion Pumper).

“People have been coming in for years to buy their trees,” said Chief Schilling. “There’s a great deal of loyalty. It’s a lot of fun when the families come in, the kids are running around picking out the trees. It’s a pretty neat experience.”

Each year, on the day before Thanksgiving, two Tisbury firefighters drive a truck donated by John Keane Excavation to Vermont, where they load up the trees. They have Thanksgiving dinner with the tree farmer, and drive the trees back the next day.

“You see the same people, you get new people,” said Nick Fullin, a member of the Legion Pumper company. “We don’t try to make a killing, we just try to make enough to do what we need to do, year after year. Christmas gets to be expensive enough.”

The money goes to extra equipment for the fire truck, as well as equipment to maintain the grounds at the Legion post.

It’s always an adventure at the Christmas Legion Pumper tree stand. Mr. Fullin said he never knows what he will see when he is selling trees.

“We had people come in last night that brought a dog,” he said. “Whichever tree the dog went up to sniff, that was the one they took. We got a tree sniffing dog and everything.”