Driving down a long dirt road near Lambert’s Cove, 18-year-old Kevin Brennan pulls over next to a few bushes that, to the untrained eye, blend in with the rest of the sea of green.

He takes a few hand-made baskets out of the car and heads into the bushes, picking wineberries from the vine and popping them in his basket (and a few in his mouth). Mr. Brennan glides across the sticky and prickly wineberry patch that happens to be interlaced with poison ivy at the roots.

At 5:30 in the morning, most of the tires on the road are bicycle wheels. Cyclists hit the pavement early, avoiding the hassles of traffic and marveling at the dawn glow that bathes the Island. Some cyclists are commuting to work, some are out for a quick pedal, some are preparing for future competitions.

Possibly the biggest, and certainly the longest, sailboat races of summer come together this weekend. Tomorrow, 74 sailboats are expected to race around the Island in the Edgartown Yacht Club’s annual Round the Island race. The race — about 52 miles in length — starts in early morning and lasts all day, taking boats clockwise around the Island.

Aquinnah

Laurence Gadd and Cecelia Elkin purchased 13 Lobsterville Road in Aquinnah from James Sanfilippo for $750,000 on July 18.

Edgartown

Ronald L. and Jill L. Sargent, trustees of 13 Atlantic Drive Realty Trust, purchased 13 Atlantic Drive in Edgartown from David M. Brush for $3,120,000 on July 16.

Richard Danielle and Joan O’Donnell Danielle purchased 22 Mockingbird Drive in Edgartown from Peter F. Baker and Mary C. O’Neill-Baker from $525,000 on July 20.

Tisbury

The Pit Stop is launching a fundraiser to add a café and reading room to the popular music destination. The moniker “destination” is not meant to confuse or be vague. It’s just that the Pit Stop is hard to categorize.

This spring Kristen Palma decided to buy a little house for sale on Ocean View Farm Road in Chilmark.

“We rented a house just down the street right before Paul got sick,” she said. “It was a strange coincidence that this house came up for sale. I think it was one of those things that was just meant to be.”

Arnold McCuller has sang with Aretha Franklin, Diana Ross, Bette Midler, Beck, Bonnie Raitt, Lyle Lovett — the list goes on and on. But mostly the list begins and ends with James Taylor.

The Vineyard is not the tiny, sunny Island that birthed the smooth and rhythmic sounds of reggae music, but it will be the one to host some of the genre’s legends on August 14.

The Wailers, most famous for their work with Bob Marley, are performing at The Lampost in Oak Bluffs at 8:30 p.m. Tickets are $32 in advance and $40 the day of the show.

Special guests include Junior Toots, Mike Martin y Los Rootsticks and Selectah Niko of One Drop Sound System. The show is presented by Nectar’s Presents and Rolling Rock.

The Sixth Annual Edgartown Board of Trade Sand Sculpture contest is Wednesday, August 1, at Right Fork, South Beach in Edgartown, to the left of the guard house.

Contestants may bring any building materials they wish, but none can be used for structural support in the final product. In other words, no sneaking in rebar foundations.

Decorations are fair game, though, but any non-biodegradable items must be cleaned up at the end of the contest.

On Friday, August 3, the Chilmark Community Center is hosting a community service event for Soaringwords, an organization that helps children with long-term illnesses and their families. Premade blankets and pillows can be decorated by community members with inspiring words and pictures. No need to bring anything — fabric pens will be provided. The finished blankets will be distributed to hospitals and Ronald McDonald Houses.