Boothbay Harbor Windjammer Days Festival



    Held in Boothbay Harbor since 1962


    File photo 

    Windjammers that have thrilled us over the years ... 

     Richard T. II, Heritage, American Eagle, Isaac H. Evans, Tabor Boy, Mattie and Mercantile, Victory Chimes, Stephen Taber, Lewis R. French, J&E Riggin, Angelique, Mary Day, Grace Bailey, Bowdoin, Nathaniel Bowditch, Thomas E. Lannon, Eastwind, Lazy Jack (in 2023: renamed Applejack), True North, Bill of Rights, Maine, Agness and Dell, Tyrone, Harvey Gamage, Mary Day, When & If, Alert, Ardelle, J & E. Riggin, Lewis R. Story, Ladona, Eagle, Sycamore, Isabella; Tall Ships of America: Adventure, Amistad, Privateer Lynx, NAO Trinidad, Spirit of Bermuda, Timberwind ... the list goes on.

    And, until 9/11, a Navy ship was sent for the Festival when one was available.


    Air shows, parades: Antique boats, traditional street event, and in 2015 - a lighted boat parade was added; Queen of the Windjammer Fleet, fireworks, street dances, The Miss Windjammer Pageant, Windjammers for Wee Mateys, Art in the Park; the Pirates of the Dark Rose, U.S. Coast Guard Station tours, Maine State Aquarium, tours of the Sail Loft/with Nathaniel Wilson, Sailmaker; musical entertainment, youth group performances, Red Cloak History Tours, American Ghost Walks tours, youth talent show/Boothbay’s Got Talent; tours of shipyards, the Windjammer golf tournament, tug of war across the harbor, crab cake cook-off, chowder and other food contests, rock skipping contest; the blessing of the fishing fleet, lobster eating contest, and cod fish relay races - all three events from the former Fishermen’s Festival.

    2023 events schedule


    Est. 1962 by Capts. David and Marion Dash 


                                                                                              ?format=500w             1492022920883








    A History of Windjammer Days 

                                      By LISA KRISTOFF /BOOTHBAY REGISTER                                   

    In the summer of 1962, Capts. David and Marion Dash were cruising into Boothbay Harbor and passed three schooners harbor-bound due to fog that were attracting a great deal of attention.

    David Dash thought one could make a day of it and include festivities for people on shore and on the schooners coming to the harbor.

    On July 10, 1963, with the help of his long-time friend and advertiser Eugene Buzzell – and $100 from the Boothbay Harbor Chamber of Commerce and $50 – from the Town of Boothbay, Dash did just that.

    Many schooner captains re-routed their schedules to participate in that first Windjammer Day. The first five schooners to the harbor were the Victory Chimes, captained by Boyd Guildout of Castine; Mary Day, Capt. Havilah Hawkins out of Sedgewick; Mattie and Mercantile, Capt. Jim Nesbitt out of Camden; Tabor Boy, Capt. George Glaesar; and Richard T. II, captained by Dash, who served as chairman of the first Windjammer Day.

    The schooners rendezvoused at Squirrel Island and sailed into the harbor, greeted by hundreds of people along the shoreline, on boats and in the harbor.

    Artist Lonnie Sisson designed and created commemorative scrolls for the passengers aboard the schooners inscribed with their names. Original framed ink drawings of each schooner by artist Peggy C. Hodges were framed and presented to each captain. On shore, passengers feasted on lobster or steak dinners in the town parking lot between Fisherman’s Wharf Inn and the R.A. Scott Company, while schooner captains attended a captains’ dinner at Fisherman’s Wharf.

    At a ceremony hosted by Franklyn Lenthall, a panel of judges chose Yale student Joan Payne to be the Queen of the Windjammer Fleet and presented her with books and an orchid corsage. Payne road aboard the Victory Chimes and broke bread with the captains.

    The queen was selected from among all female passengers on one of the five vessels by judges Jean Blakemore, Joe Holland and Walter Wright.

    Windjammer Day 1963 included an aquatic show organized by Pierce Marine Service in front of its marina on the east side; key chains bearing numbers set afloat in the harbor provided boaters an opportunity to win prizes, from boat cushions to ski tow rope.

    Folk singers Frank and Pete put on a hootenanny in the town parking lot and the Choralaires of Boothbay Harbor (Marion Dash, Irene Farnham, Diane Michaels, Martha Vaughn, John Hartford, Herbert Godfried and Malcolm Pierce) sang sea songs.

    To enable as many people to view the schooners from the sea as possible, Dash and Capt. Eliot Winslow of Southport gave boat rides to raffle winners.

    The raffle prizes included the first Windjammer Day oil painting of a three-masted schooner by Peggy C. Hodges, tickets to the Boothbay Playhouse production of “Miranda,” a sea chest, a 4-month-old Cocker Spaniel, a gazing globe, Boothbay Register subscriptions and a “fine pair” of binoculars, along with the grand prize, a one-week sail aboard one of the schooners.

    A front page story in the July 18, 1963, Boothbay Register bore the headline: “Windjammer Day Celebration Apparent Success in Region.”

    “The streets, sidewalks and waterfront were be-speckled with visiting tourists and year-round residents…” the Register reported. “The harbor was crammed with boats of all sizes and descriptions…”

    The Boothbay Harbor Region Chamber of Commerce sent more than 800 press releases to national media. White House Press Secretary Pierre Salinger put out a press release through the White House Press Association.

    Southport resident Robert MacKusick researched and wrote a history of windjammers for a special section of the Register, a tradition that has grown with the festival.

    The schooners’ entrance into the harbor was covered by news stations WGAN and WCSH with approximately three minutes of coverage of the event on their 11 p.m. newscasts. Windjammer Day was also covered by the Department of Economic Development and stringers for the Associated Press and United Press International.

    Following the event, the Chamber office reported an increase in calls about lodging in the area due to all of the publicity Windjammer Day received. The Chamber elected to make Windjammer Day an annual event to be held the second week in July, and the schooner captains indicated they would be interested in participating in coming years.

    “The first Windjammer Days was really a very simple event,” Dash told the Register in 1963. “It involved a lot of community participation and a limited budget. We had an original concept. Our goal was to present a simple, wholesome re-creation of the old days.”

    Snapshots through the decades

    The Miss Windjammer Pageant was held from 1967 through 1987 and was an official preliminary Miss America pageant. It was open to young women age 16 to 26, who were year-round or summer residents of Lincoln, Knox, Waldo, Kennebec or Androscoggin counties.

    The contestants could not have ever been married and had to be planning to continue their education. The pageant followed the same format as Miss America: contestants were interviewed by the judges, modeled swimsuits and evening gowns, and presented a talent in no more than three minutes. The first Miss Windjammer was Elizabeth “Betsey” Barrett and the last was Amanda Crafts.

    Each year, the winner was crowned by a former Miss America.

    In 1987, the festival was still a one-day event. That year, for the first time, a male contestant was to be crowned Captain Windjammer. However, no one signed up for a chance at the honor and Miss Windjammer continued to reign alone.

    The Windjammer Days Committee dropped the 20-year-old pageant in 1988 in favor of a Windjammer Review, to include acts from around the region. The review was held before a standing-room-only crowd at the Opera House.

    The Windjammer Days of the 1980s included an air show by Jim Parker with flybys by military aircraft and craft from Owl’s Head Transportation Museum.

    The ’80s saw the creation of the Windjammer rum cocktail (1 oz. white rum, 1/2 oz. Southern Comfort, 1/2 oz. Blue Curacao and 1/2 oz. simple syrup, with equal parts orange and pineapple juices and lemon mix, shaken well to create a frothy top). The Boothbay Harbor Region Chamber of Commerce issued a commemorative glass (perfect for serving the cocktail): 15 1/2 oz. medium blue semi-tulip shaped with a sham bottom bearing the chamber logo in chalk white.

    The first Windjammer Days print was created from a watercolor by East Boothbay artist Earle B. Barlow, who described what he believed the painting should convey: “Although there are many activities which are part of the Windjammer Days celebration, these activities center around the beautiful vessels, and especially their arrival at the inner harbor under full sail… In creating a painting that would capture the essence of these dramatic moments, it seemed of particular importance first that the schooners should be presented in a way to convey the excitement they evoke… the schooners be represented not just as pretty boats, but with an authenticity that would identify specific vessels…”

    An article in the July 3, 1986, issue of the Register described some of the many ways the festival had been described. “Someone once said (Dash) had taken the concept of a museum and made it come to life again. In a more succinct manner, a fisherman commented on Windjammer Day, ‘Looks like 40 years ago.’”

    1988 marked the first time the festival had national and international coverage when NBC came to town. Willard Scott was scheduled to do the reporting, but at the last minute the network sent Joe White instead.

    The first antique boat parade took to festival waters in 1989.

    By the 1990s, in addition to the street parade, fireworks and a few musical concerts, there were softball games, a street dance at the town landing with live music, youth events on the ball field and U.S. Coast Guard search and rescue demos.

    The first golf tournament was in 1991, called the Windjammer Charity Celebrity Open at the Boothbay Country Club, and would become one of the top annual fundraising events for Special Olympics Maine. The event was moved to September in 2000 and is now known as the Boothbay Charities Classic.

    In 1996, 34 years after they founded the festival, the Capts. Dash served as the Mariner’s Mardi Gras Street Parade Grand Marshals.

    Over the years the festival has included open houses aboard some of the visiting vessels, band concerts on the library lawn and waterfront park, garden club tours, chowder and dessert contests, pancake breakfasts, a photo contest, waterfront food vendors, tours of the U.S. Coast Guard Station, tours of shipyards, including Washburn & Doughty and Hodgdon Yachts, baseball/softball clinics for kids, softball games, street dances, a Bang & Go sailboat race, church suppers and street dances.

    Over its first 50 years, the number of visiting schooners has varied; several years there were close to 20 in the harbor.

    In 1994, 12 schooners were expected, but fog, southwest winds up to 30 knots and six- to eight-foot swells prevented all but the schooners Bill of Rights from Philadelphia and Maine out of Bath from attending the festival.

    That year, a wind-driven thunderstorm caused small rivers to run down Boothbay House Hill Road into the waterfront parking lot. After the storm passed, Boston-based band Heavy Metal Horns went on with their show, but the fireworks were cancelled. They were saved for an extra special Fourth of July display.

    Fireworks became a fixture of the celebration in 1984. However, the first time fireworks played a part in Windjammer Days was 1970. At that time, the festival was held in July, and due to inclement weather conditions on the Fourth, the fireworks were delayed. Windjammer Days was moved to late June in 1990.

    “It is an awesome event. I never realized that it would come to this. People in town have grown up with it, and the people on the boats plan their vacations around it… In the beginning I got a lot of flack about parking – I guess some things will never change,” Dash told the Register in 1987. “For Marion and me, it’s a thrill to sail between two boats and feel the power of the sailing vessels.”

    And then in 2013 ...

    Local group chosen to run Windjammer Days (excerpts)

    By Ryan Leighton

    On December 17, the Boothbay Harbor Region Chamber of Commerce Board of Directors voted to award the bid to the Friends of Windjammer Days committee.

    Mark and Dianne Gimbel met with Chamber board members two days later to discuss taking over the region's summertime festival.

    The Gimbels, representing the Friends of Windjammer Days committee, were just one of two organizations who submitted proposals. The other party interested was a Chamber member that had several business ties to the Midcoast region, but the Chamber chose to award the local group who had the prior experience volunteering with Windjammer Days.

    In an email to the Boothbay Register, Dianne Gimbel wrote, “We are happy to be chosen and we are discussing the conditions with the Friends (of Windjammer Days). We are looking forward to a really great WJD 2014.”

    Peter Ripley, who has worked the Boothbay Harbor waterfront since 1972, was recently appointed to the Friends of Windjammer Days Board of Directors. Ripley responded in an email that he was very happy with the Chamber's decision to award the bid to the local group.

    “The conditions made by the Chamber were not completely unexpected and the Friends of Windjammers Days are continuing discussions with the Chamber,” Ripley wrote. “Most of all we are all looking forward to a fantastic WJD 2014!”


    The Friends of Windjammer Days are a 501c3 non-profit group of volunteers who have come together to continue the tradition of Windjammer Days in Boothbay Harbor. They have committed to maintaining the heritage of this maritime event to enhance the Boothbay Region community and the experience of maritime Maine.

    Owner/Captain John Foss
    Homeport - Rockland, ME

    Foss’ new ship Eagle, is a 34' Murray Peterson Schooner rebuilt from a 1927 Alden Malabar Junior. Capt. Foss is the former owner of American Eagle, which he bought in 1984 and completely restored. he was a stalwart in his long term support of Windjammer Days. Now he gets to keep his love of sailing alive without the daily work of a cruising schooner business. 

    Captain Fred Bowers
    Homeport Wiscasset

    The Sycamore is a steel, two -masted schooner build by Fred Bowers over 16 years.  It is a steel representation of a pinky schooner, one of two vessel designs originally used in Maine's fisheries in the early 19th century.

    Captain Seth Salzmann
    Runs charters out of Salem, MA and Key West

    When and If is a yacht designed by John Alden and commissioned by then Colonel George S. Patton, a widely regarded American war hero. It was built in 1939 as a private yacht by boatbuilder F.F. Pendleton in Wiscasset, Maine.

    It was constructed of double planked mahogany over black locust frames and an oak keel.

    Captain Andrew Grainger
    Homeport Boston, Massachusetts
    Summer Home Pemaquid, Maine

    True North was built in 1939 by Goudy & Stevens in East Boothbay. She is an Alden Schooner, 56 feet overall, one of  the approximately 45 Alden schooners in existence.



      Windjammer Festival 2023