For a whole week in August, the waters around Nantucket are full of boats ready to race in one of the most varied and challenging sailboat racing locations in the world. Nantucket Race Week hosts competitions for everything from small dinghy classes to kiteboards, Wianno Seniors, and even large schooners. Nantucket Race Week is hosted by the Nantucket and Great Harbor Yacht Clubs to benefit Nantucket Community Sailing.

Started by some sailors as a gift to their favorite restaurateur, the Opera House Cup has grown into one of the premier events for wooden sailboat racing. OHC is one of the oldest wooden boat races in the world, and culminating race of Nantucket Race Week.

Every Memorial Day weekend, one of the largest sailing races in the world takes place between Hyannisport and Nantucket.

Three friends set out in 1972 to find out who had the fastest boat. It was a a very foggy day, and ended up sailing in circles for a while. The eventual race gained its unusual name at this point– one of the three skippers asked, with an accent, ‘Where the Figawi?’

The Hyannis Regatta is an annual two-day series of races for PHRF Ocean Class and One-Design Classes. 2025 will be the 82nd year that this event has been organized by Hyannis Yacht Club.

Depending on the number and variety of entries, sailing takes place using three to four race circles either in Lewis Bay or in the more challenging Nantucket Sound, off Hyannis Port.

The Hyannis Youth Regatta began as a part of the Hyannis Regatta. Primarily the small boat classes such as Beetlecats, 420s, Lasers, Optis and 505s, were sailed by junior sailors. With this extraordinary expansion of the youth category, it was divided out of the Hyannis Regatta, and has now had become a world class regatta of its own.

The annual Chatham Regatta, held at the Chatham Yacht Club on Pleasant Bay, lays claim to the title of oldest and largest free regatta on Cape Cod. It began in 1921, and today at least 9 different boat designs are eligible to race.

The Vineyard Cup Regatta is held on the waters of Nantucket Sound and Vineyard Sound, with racing on Friday through Sunday in early July. The regatta is hosted by Martha’s Vineyard Shipyard. All funds raised through the regatta go towards Sail Martha’s Vineyard’s on-and off-the-water marine education programs. There are divisions for Herreshoff 12 ½, Catboats, PHRF-rated Spinnaker and non–Spinnaker boats, and a Classic Division.

The H-Class Association was formed to promote and preserve the Herreshoff 12 ½.

In 1928, they began the H-Class Championships. Since 1973, the Championships have rotated between the five affiliated yacht clubs: Beverly, Buzzards, Edgartown, Quissett, and Shelter Island. It is open to existing wooden 12 1/2s, and the fiberglass Doughdish.

This year the Championships will be hosted at the Buzzards Yacht Club.

In 2023, Buzzards Yacht Club and Ballentine’s Boat Shop hosted the first annual Bill Harding Memorial Regatta. This regatta is open to Herreshoff 12 1/2s and Stuart Knockabouts, and is a celebration to honor Mr Harding's memory and his contributions to these two historic designs.

The mission with this regatta is to build a yearly tradition that will not only help to grow the classes, but to also foster more friendship, competition, and fun between local yacht clubs. This regatta takes place in early August.

The first Edgartown Regatta was held in 1924. It was so well received and attended it evolved into an annual competition which attracted hundreds of boats. The main event is a ‘Round the Island’ race, which was first a part of the regatta in 1938. Today’s race is approximately 55 nautical miles and takes most of a day. There are strict standards for measurements and equipment, and cell phones and GPS are forbidden. This race turned 102 in 2025!