What do a media mogul, movie maker and American President have in common? Taking part in yacht racing, one of our nation’s oldest sports, and New England, the cradle of this sport in America. Ted Turner won the 1977 America’s Cup in Newport. Roy Disney sailed from Newport to Bermuda with record-breaking speed in 2002. And in 1936, JFK earned a winner’s cup racing Stars in the Hyannis Port Yacht Club race to Edgartown.
With more than 6,000 miles of shoreline, survival built on the sea from olden days of fishing and trading to today’s seasonal tourist dollars, it’s a natural that racing sailboats is a time-honored tradition and rite of passion for most New Englanders. Many sailors here boast blood as blue as the surrounding seas, yet everyone can find a home to race. Here’s a sampling of some of the region’s best-known regattas.
MAINE
Camden Classics Cup
July 28-30
Competition and camaraderie combine in this relative newcomer event sailed in Penobscot Bay and celebrated shoreside in downtown Camden. Over 100 sailboats, everything from vintage yachts to very fast one-designs like J/46s and J/42s, race. Classes are available for day sailors and cruising yachts, too. “Dockage at Lyman-Morse is included in the race fee, so the party starts ashore when the racing ends,” says organizer Mackenzie Lyman, who adds the marina operator and boat-builders have rebuilt the waterfront after a fire in 2020. Spectators can have just as much fun. Maine’s Wind- jammers offer two-hour tours to view the racing, while landlubber’s best bet is watching the parade of sail as dressed yachts with costumed crew parade through Camden harbor on the morning of July 30. camdenclassicscup.com
Boothbay Harbor Yacht Club Annual Regatta & Shipyard Cup Classics Challenge
July 23-24
A trend toward classic yacht racing and a nod to the area’s deep sailing roots combined for the first time last year at the Shipyard Cup. This new addition to the nearly 50-year-old annual regatta put lots of eye-candy on the water. The 1926-built NY-40, Marilee and 1937-constructed 12-meter America’s Cup contender, Gleam, plus classic Boothbay Harbor one-designs like the 21-foot, Geerd Hendel-designed, 1938-launched sloops, are expected back this year along with contemporary race yachts. “We invited several America’s Cup contenders to join Gleam this year on the start line,” says co-chair Bob Scribner. Spectators can observe from Spruce Point, McKeown Point or Southport. A narrated parade of participants in the inner harbor starts at 10:00 a.m. on July 24. boothbayregatta.com
MASSACHUSETTS
Helly Hansen Sailing World Regatta Series – Marblehead
July 28-31
The 1889-founded Marblehead Race Week joined with National Offshore One-Design concept a few years back, and the result is close to 200 boats racing. “We now have all our regular classes like J/70s, Rhodes 19s and Viper 640, plus there are usually one or two guest classes like RS21s, Skuds, 2.4’s and J/24s, that hold regional championships as part of the week,” says Leslie Rousseau, race committee chair for the host Boston Yacht Club. “We expect to see the return of Jud Smith, two-time Rolex Yachtsman of the Year and local J-70 favorite.” Spectators on land can get a bird’s eye view of the racing from Chandler Hovey Park on Marblehead Neck. Those with a fast center console can watch the boats line up to start off Turkey Point in Middle River or set their chutes at the windward mark in Middle River. sailingworld.com/regatta-series-marblehead
Edgartown Race Weekend
June 23-25
Since 1938, celebrity-studded Martha’s Vineyard is home to this week of combo coastal, offshore and round-the-island racing hosted by Edgartown Yacht Club. “The history, charm and summer activity on Martha’s Vineyard is a meaningful draw, in addition to fantastic wind and ideal sailing conditions,” says Alex Nugent, one of the event’s co-chairs. “Plus, we typically host a big welcome party that’s sponsored by Mount Gay Rum.” New is the ‘Round-the-Sound series of races, which features 20-some nautical mile coastal sprints around Vineyard Sound and Nantucket Sound and replaces the around-the-buoy series. There’s monohull and multihull, racing and cruising, double-handed and many-handed entrants including teams from state and federal service and maritime academies. edgartownyc.org
Nantucket Race Week
August 13-21
Nine days of racing, parties and awards ceremonies take the concept of race week to the extreme. There’s something afloat for everyone: kids in Optis and 420s, women in Rhodes 19s, kiteboarders, radio-controlled model boats and some of the country’s top sailors competing in high-performance big boats and classic wooden yachts. “This year we celebrate the 50th Opera House Cup Regatta, the grand dame of classic wooden boat regattas. The Cup, named after a legendary Nantucket restaurant, attracts some of the finest wooden boats on the East Coast and Europe. There is a big awards party on the beach after the race,” says Diana Brown, chief executive of Nantucket Community Sailing. The Parade of Wooden Boats offers a brochure that describes each participating boat. The public can watch the parade from Brant Point Beach. nantucketraceweek.org
RHODE ISLAND
Annual Regatta
June 10-12
Hosted by the New York Yacht Club (NYYC) out of its facilities in Newport, this is North America’s oldest continuously held sailing event going on its 168th year. The format features two days of buoy racing, prefaced by a race around Conanicut Island. The sight of 100-plus spinnakers running north in the West Passage of Narragansett Bay from Fort Adams, Castle Hill or Beavertail Light is breathtaking. Entries are invited to one-design classes, and boats more than 24 feet race under a variety of handicaps. “The Annual Regatta is one of my perennial favorites,” says Paul Zabetakis, NYYC commodore and a regular participant on his Swan 42, Impetuous. “The race management is impeccable with multiple course configurations. Few other venues offer the perfect combination of offshore racing in Rhode Island Sound and inshore racing on Narragansett Bay.” The Saturday night regatta party is one of the biggest occasions of the Newport regatta season with sailors converging on Harbour Court for cocktails and dinner. nyyc.org/168th-annual-regatta
Newport to Bermuda Race
June 17
The lawn at Castle Hill Inn in Newport and Fort Wetherill in Jamestown are ringside seats to watch nearly 200 vessels start in the East Passage on a 635-mile passage south to Bermuda. “Fort Adams State Park also provides close-up views of many of the boats as they depart from Newport Harbor. The fleet then sails past Brenton State Park as it clears Brenton Reef and turns to the southeast. Charter boats and private yachts assemble to watch the start from the water as well,” says John Burnham. It’s one of the oldest regularly scheduled ocean races, happening biennially since 1906. This year, three high-speed multihulls – two MOD 70s, Argo and Snowflake, and the 78’ trimaran Ultim’Emotion 2 – are entered, and each has a good chance of breaking the elapsed time race record of 34h:42m:53s set in 2016 by the 100’ maxi yacht, Comanche. bermudarace.com
Ida Lewis Distance Race
August 18-20
The fleet goes where the wind blows. “The Ida Lewis Distance Race is like no other in that the Race Committee chooses from among four different courses, based on the weather. Each course incorporates some of the most storied cruising grounds in New England and is just long enough for the fleet to be offshore overnight, yet not so long to prohibit inviting family and friends to join for a first-time adventure,” says Anselm Richards, event chair. The goal: get about 60-some teams to compete on race boats 28-foot and longer in double-handed, youth, collegiate and different handicap classes back to the dock in under 24 hours. The start happens off Fort Adams and ends inside Newport Harbor, where each team is handed a congratulatory bottle of Prosecco. ilyc.org/distancerace
CONNECTICUT
Block Island Race
May 27
Stamford is the start of this Memorial Day weekend regatta that for many sailors kicks New England’s offshore racing season. “The 186-nautical mile course down Long Island Sound and around Block Island and back also acts as a ‘warm up’ for many teams that are racing some two weeks later in the Newport to Bermuda Race,” says Kate Wilson Somers, who handles media for the event. The race marks its 75th anniversary this year and is organized by the Storm Trysail Club, based in Larchmont, NY. stormtrysail.org/regattas/block-island-race
Cedar Point One Design Regatta
June 4-5
A 20-year+ tradition on the first weekend in June, this one-design keelboat event hosted out of the Cedar Point Yacht Club in Westport, CT, can draw as many as 800 competitors on over 100 boats. The key is that all the boats in a class are the same; no handicap scoring is needed. This makes it easy to watch, as first over the finish line is the winner. “Currently, the event is open to J70, J88, J105 and J109, and Beneteau 36.7 fleets, but other fleets are welcome if they meet the requirements,” says Joyce Oberdorf, who handles the club’s communications. cedarpointyc.org/odr
