Sailing regattas are a New England summertime tradition. From July to early September, thrilling sailboat races take place from Nantucket to Newport every weekend. No other region quite compares to New England’s yachting community.
And of all sailboat races, classic regattas – featuring vintage, wooden and Spirit of Tradition sailboats – are some of the most exciting to watch.
Not only are the classically styled yachts some of the most beautiful boats in the world, the racing is inspiring, conjuring up the spirit of yachting lore. In other words, attendees get treated to the best in summertime entertainment. The races are a thrill to watch, and the dockside social soirees, awards ceremonies and parties enable attendees to chat with New England’s finest yachtsmen. For yachters, there isn’t a better way to spend a summer weekend in New England.
Which sailing regattas should you attend? Worldwide Boat has the insider’s scoop on some of New England’s most prestigious summer sailboat races. Try to make it to a few – and of course, a sailboat charter for race day offers the best seat to take in all the thrilling action.
Classic Regattas to Catch every Summer
1. Vineyard Cup – Martha’s Vineyard, MA – (July)
Held in Martha’s Vineyard, this regatta features more than 100 participating yachts, and a full slate of races over three days. The event – which was launched in 2006 – is sponsored by Sail MV, and it’s quickly become one of New England’s premier regattas. Not only is the racing spectacular, attendees can enjoy a wide range of onshore events. Although this isn’t strictly a classic regatta – there many different classes of boats and races courses – the Vineyard Cup is a must-see for classic yacht enthusiasts.
2. Castine to Camden Yacht Race – Castine, ME – (August)
The Castine Classic Yacht Race – part of three days of regattas in the 2018 Wooden Boat Series – takes place in Maine’s stunning Penobscot Bay, an inlet in the Gulf of Maine. Specked with islands more than 200 miles and spectacular harbors, the bay offers the best in Maine yachting. The Castine to Camden race puts yachters on a 20-mile course across the Bay, from Castine to Camden. Castine Yacht Club, the race’s sponsor, opens the regatta to classic and Spirit of Tradition monohulls over 28’.
3. Camden Classic Yacht Regatta – Camden, ME – (August)
For more than 30 years, classic yachts have gathered at the Camden Yacht Club for the annual Camden Classic Regatta. Featuring a challenging 15+ mile course, the yacht runs from Camden to Brooklin, ME. This, along with the Castine and Eggemoggin races, make up a wonderful three days of classic yacht racing on Penobscot Bay.
4. Eggemoggin Reach Regatta – Brooklin, ME – (August)
Since 1985, the Eggemoggin Reach Regatta has run each summer during the first weekend in August. And since its launch, the race has grown significantly, from 13 wooden yachts in 1985, to more than 125 boats in recent years. The field typically includes boats of various sizes – from 25’ to 90’ – and takes racers along a challenge 15-mile course in Penobscot Bay. If you love classic yachts, you want to be on Penobscot Bay during the first weekend in Austin.
5. Corinthian Classic Yacht Regatta – Marblehead, MA – (August)
Corinthian is a name synonymous with New England sailing. For more than 125 years, the Corinthian Yacht Club has called Marblehead, MA home, and in that time, they’ve produced numerous racing champions including several America’s Cup defenders. The Corinthian Classic Yacht Regatta was started nearly 40 years ago, and it’s become of the largest celebrates of “classic yachts and characters.” Just as speculator as the racing, though, is the onshore atmosphere, another compelling reason to go.
6. Nantucket Race Week – Nantucket, MA – (August)
Nantucket Race Week runs for nine days in mid-August, and features races in numerous classes. Yet, one of the week’s most exciting races is the Nantucket Regatta (held on August 18). The race was first run in 1930, but recently underwent restructuring in 2016. Open to 24+ foot classic wooden yachts, the regatta is part of the North American Panerai Classic Yachts Challenge Series. And it’s certainly one race you will want to catch during the week.
7. Opera House Cup – Nantucket, MA – (August)
The Opera House Cup is the oldest classic sailboat race on the East Coast, having started more than 40 years ago in 1973. A joy to watch, the Opera House Cup draws a fleet up roughly 100 vintage yachts – offering a unique look at many different styles of classic boats.
8. Herreshoff Classic Yacht Regatta – Bristol, RI – (August)
The Herreschoff Regatta – held each year in Bristol, RI – was named after the Herreschoff Manufacturing Company, a storied yacht builder that produced several America’s Cup defenders. In fact, many classic yachts feature Herreschoff designs. The classic regatta – part of the Panerai Series – takes place in the picturesque Narragansett Bay on Friday, with its sister race the Newport Classic taking place on Saturday. Throughout the weekend, attendees are welcomed to cocktail hours, expos and plenty to see and do.
9. Newport Classic Yacht Regatta – Newport, RI – (August)
Newport is a classic New England yachting town – one of the largest yacht charter ports in New England. And with its long history in sailing, it makes sense Newport is one to one of the East Coast’s most exciting classic regattas. Since 1980, the Newport Classic race has taken place in the southern reaches of Narragansett Bay. Part of the Narragansett Bay Classic Yacht Rendezvous – along with the Herrschoff – the race starts from Bristol to Newport, followed by racing near Newport.
10. Indian Harbor Yacht Club Classic Yacht Regatta – Greenwich, CT – (September)
A recent addition to the classic regatta summer series, the Indian Harbor Classic Regatta takes place on Long Island Sound. The regatta’s sponsor – Greenwich, CT’s Indian Harbor Yacht Club – opens the race to classic and Spirit of Tradition yachts, and hosts awards dinners, cocktail hours and parties throughout the weekend.
Charter a Sailing Yacht for Regatta Season
A classic sailboat regatta is a summertime tradition in New England. And there’s no better way to experience the action, than aboard a luxury charter yacht. Follow the action live and have a home base to host guests aboard in the evening.