Size Matters takes home the prize for the Oh My God That’s a Big Boat race. ISLANDER PHOTO BY MALACHY FLYNN

Winter Harbor hosts 58th annual Lobster Boat Race 

Foolish Pleasure takes first place in the Gasoline Class D and Free for All races.

WINTER HARBOR — Crowds gathered at the dock in Winter Harbor on Saturday for the start of the 58th annual lobster boat race hosted by the town. The races ran during the Winter Harbor Lobster Festival, which held a crafts fair at the fire station and lobster dinners at the Masonic Lodge. 

The Winter Harbor Lobster Boat Race is the first of the August races, followed by the Merritt Brackett race that took place in Pemaquid on Aug. 14, the Long Island race on Saturday, Aug. 20, and the MS Harborfest race in Portland on Sunday, Aug. 21. 

On Aug. 13, there were 29 races over the course of the day for different classes and categories of boats. Ninety-seven boats registered for the races, across all classes and categories, with several appearing in multiple races.  

After the races, participants and spectators gathered near the dock for the award presentation, where the winners of each race were given a trophy featuring a hand-blown glass anchor. Other prizes were awarded based on a drawing of all the boats in the races and included several cash prizes, $20,000 worth of fuel, chainsaws, tool sets and knives from Maine Knife Company.  

Heather Thompson’s boat, Gold Digger, won the Lady Skippers race, as well as Diesel Class J. David Myrick’s boat, Janice Elaine, won the Diesel Free for All as well as Diesel Class K. Mark Freeman’s boat, Foolish Pleasure, won the Gasoline Free for All and Gasoline Class D. Dixon Smith’s boat, Size Matters, took home first place in the Oh My God That’s a Big Boat race, and Jeff Eaton’s boat, La Bella Vita, won first place for Fastest Lobster Boat. 

Race results 

Work boats 24 feet and under 

Race 1 – Class A, Inboard, Outboard or Outdrive, any hp, must have a working hauler 

  1. Daddy Didn’t Buy It, Nathaniel Robinson 
  2. Little Miss Abbie, Mark Piper 
  3. Mini Me, Jett Joy 


Gas-powered work boats 24 feet and up 

Race 2 – Gasoline Class A 

No entrants 

Race 3 – Gasoline Class B, V8 up to 375 cid, 24 feet and up 

  1. Empty Pockets, Roy Hadlock 

Race 4 – Gasoline Class C 

No entrants 

Race 5 – Gasoline Class D, 386 cid and over, 24 feet and over (non-working racer) 

  1. Foolish Pleasure, Mark Freeman 

Race 6 – Gasoline Class E 

No entrants 

Diesel-powered work boats 24 feet and up 

Race 7 – Diesel Class A, up to 235 hp, 24 to 31 feet 

  1. Prince of Peace, Brian Tredwell
  2. Black Thundah II, Brandon Murphy
  3. Southern Belle, Cole Faulkingham 

Race 8 – Diesel Class B, up to 235 hp, 32 feet and over 

  1. Megan Suzanne, Emmett Mosher
  2. Mr. Lucky, Kit Johnson
  3. Caitlyn, David Schlaefer 

Race 9 – Diesel Class C, 236 to 335 hp, 24 to 33 feet 

  1. Last Design, Roy Fagonde
  2. Navigator, Michaela Byers
  3. Sh*t 4 Brains, Lance Kennedy 

Race 10 – Diesel Class D, 236 to 335 hp, 34 feet and over 

  1. Wrecking Crew, Ivan Libby
  2. Ellen Louise, Conner Rossi
  3. Bonnie’s Brats, Roy Whalen 

Race 11 – Diesel Class E, 336 to 435 hp, 24 to 33 feet 

  1. Audrey May, Randy Durkee
  2. High Voltage, Daniel Sawyer
  3. Catherine Elizabeth, Allan Johnson 

Race 12 – Diesel Class F, 336 to 435 hp, 34 feet and over 

  1. Faith Melle, Winfred Alley Jr.
  2. Sunshine Chalet, Brian Strout
  3. Rich Endeavor, Colyn Rich 

Race 13 – Diesel Class G, 436 to 550 hp, 28 to 35 feet 

  1. Right Stuff, Dana Beal 

Race 14 – Diesel Class H, 436 to 550 hp, 36 feet and over 

  1. Melynda M., William Coombs
  2. Bethany Grace, Dan Beal
  3. Tuna Wishing, Jason West 

Race 15 – Diesel Class I, 551 to 700 hp, 28 to 35 feet 

  1. Obsession, Ryan Lemieux
  2. Triple X, Colby Oakes
  3. Margaret E., Patrick Faulkingham 

Race 16 – Diesel Class J, 551 to 700 hp, 36 feet and over 

  1. Gold Digger, Heather Thompson
  2. Fifth Generation, Mac Kelley
  3. Easy Money, Nathan Thompson 

Race 17 – Diesel Class K, 701 to 900 hp, 28 feet and over 

  1. Janice Elaine, David Myrick
  2. La Bella Vita, Jeff Eaton 

Race 18 – Diesel Class L, 901 hp and over, 28 feet and over 

  1. Marie’s Nightmare II, Jeremy Beal 

Race 19 – Diesel Class M(A), 40 feet and over, up to 500 hp 

  1. Miss Tonia, David Merchant
  2. Old School, Chris Pope
  3. Miss Rebecka, Josh Trundy 

Race 20 – Diesel Class M(B), 40 feet and over, 501 to 750 hp 

  1. Kimberly Ann, Eric Beal
  2. Miss Madelyn, Jason Chipman
  3. Alexsa Rose, Matt Shepard 

Race 21 – Diesel Class N, 40 feet and over, 751 hp and over 

  1. Terrie J., Todd Pinkham
  2. Natalie E., Dana Beal
  3. Pier Pressure, Jason West 

Outlaw classes 

Race 22 –Class O 

No entrants 

Race 23 – Class P, Oh My God That’s a Big Boat, 44 feet and over 

  1. Size Matters, Dixon Smith
  2. Kayla Ann, Josh Beal
  3. Hammer Down, Jared Coffin 

Race 24 –Wooden Boat Race A 

No entrants 

Race 25 –Wooden Boat Race B 

No entrants 

Race 26 – Lady Skippers, must have a lobster license 

  1. Gold Digger, Heather Thompson
  2. Navigator, Michaela Byers
  3. 51, Robin Faulkingham 

Race 27 – Gasoline Free for All 

  1. Foolish Pleasure, Mark Freeman 

Race 28 – Diesel Free for All 

  1. Janice Elaine, David Myrick
  2. La Bella Vita, Jeff Eaton
  3. Gold Digger, Heather Thompson 

Race 29 – Fastest Lobster Boat 

  1. La Bella Vita, Jeff Eaton
  2. Janice Elaine, David Myrick
  3. Foolish Pleasure, Mark Freeman 
Malachy Flynn

Malachy Flynn

Reporter Malachy Flynn covers news on the Schoodic beat, which includes the towns of Eastbrook, Franklin, Hancock, Sorrento, Sullivan, Trenton, Waltham, and Winter Harbor. He also reports on the town of Tremont on Mount Desert Island. He welcomes tips and suggestions about stories in the area. To contact Malachy with tips or questions, email him at [email protected].
Malachy Flynn

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