Possibly the biggest, and certainly the longest, sailboat races of summer come together this weekend. On Saurday, 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.

The second annual Cool Pool Parties fundraising event to benefit the YMCA is this Saturday, July 28, from 7 to 10 p.m.

The idea is simple and yet ingenious. Guests are invited to choose one of three private Vineyard properties to relax poolside and enjoy a party matched to a particular theme.

Batch on Hatch is hosted by Kathy and Jim Gidwitz and takes place in Vineyard Haven. This party features music by Andy Suzuki and food by Kitchen Porch catering.

The Vineyard House, the Island's only sober housing facility, will host its annual Water Tasting by the Sea fundraiser on Thursday, July 26 at the Boch family estate on Katama Bay from 5:30 to 7:30 p.m. Gourmet water varieties, such as Nestle's blood orange and grapefruit sparkling beverages, as well as L. Knife and Son’s Saratoga Spring water, will be available for sipping. The fundraiser also features music by Johnny Hoy and the Bluefish, food by Tea Lane Caterers and a silent auction.

Want to mingle with the cast of The Wire while showing your support for President Barack Obama's re-election campaign? On August 15, longtime Obama supporters and Island residents Judy and Ron Davenport will host a fundraiser at their home featuring the cast of the hit HBO show. The president is not expected to attend.

The Vineyard Youth Tennis program, which provides free tennis lessons and court time at its Oak Bluffs facility, is celebrating its 10th anniversary on Saturday, July 21 with a professional tennis exhibition, tennis games and prizes, a kids' carnival with clowns, as well as magicians and face painting. Festivities begin at 9:30 a.m. For more information, call 508-693-7762.

Keep your eyes on the water today where hundreds of sailboats, from schooners to catboats to modern design racers, are partaking in the Vineyard Cup. Races are based out of Vineyard Haven harbor, but you also can catch a glimpse of the action from the East an West Chop Lighthouses, Eastville Beach, State Beach and at the entrance of Lake Tashmoo.

The Vineyard Cup is an annual benefit for Sail Martha’s Vineyard, which provides sailing lessons and instructions to Island youth. 

The Martha’s Vineyard Museum is hosting two agricultural fair photo collection days to help with a new book being created by Susan Klein and Alan Brigish. The authors are on a quest to find a variety of images taken at the fair over the years for inclusion in the upcoming book. Photos will be scanned and returned immediately.

The collection days will be held on Friday, Jan. 6, from noon to 1 p.m. and 4 to 6 p.m. and again on Saturday, Jan. 7, from noon to 3 p.m. Both dates take place at 59 School street in Edgartown.

Volunteers at this year’s Christmas Bird Count spotted 119 species, according to Gazette bird columnist Susan Whiting, a cocompiler of the annual event on the Island. Though the species count was similar to recent years, the number of individual birds spotted, 21,730, was lower than in most counts of late. In 2010, only 15,926 individual birds were counted, due to few participant, but in 2009 32,114 individual birds were recorded. In 2008, that number was nearly 83,000.

Tisbury Democrats are looking for delegates to send to the 2012 Massachusetts Democratic convention next June. The town Democrats are planning a caucus in February to elect three delegates and three alternates.

The caucus is open to all registered Democrats in Tisbury, but you must be registered by Friday, Dec. 30, in order to be eligible.

The caucus will be held on Feb. 25 at Rocco’s Family Style Italian Restaurant. Delegates will participate in selecting candidates to compete for the Democratic nomination to the U.S. Senate.

Vineyard hotelier Mark Snider is expanding his interests to Nantucket, where he is set to buy The Point Breeze, a historic hotel on the Vineyard’s sister island. Mr. Snider owns the Winnetu Oceanside Resort at Katama in Edgartown. He is also president of Stanmar Inc., a building company in Wayland.

The Nantucket Inquirer and Mirror reported on Thursday that Mr. Snider has signed a deal to buy the Point Breeze from TD Bank, which has owned the hotel since it fell into foreclosure two years ago. Purchase price has not been disclosed.