In addition to the series-specific awards presented by the MRA and/or the host yacht club for top-place finishes, Fleet #5 has its own group of awards and perpetual trophies, most of which it presents at the annual awards banquet held each fall. Each of these has a story, and is representative of the long history of Fleet #5.
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Trophy Winners
| Year | Outstanding Crew (Richie Santos) | Most Improved | Rookie of the Year | Nick Nichols (Season Overall) | Race Week | President’s Trophy | Charlie Barr (Twilight Series) | Hallawell (family) | Spittoon |
| 2024 | Team Lane / Heffernan | Adam Roberts | Adam Roberts | ||||||
| 2023 | Christina Pandapas | Rich Denton | Marine Regnault | Christina & Kim Pandapas | Hooks | Timmy Dittrich | The Regnault family –Marine, Alex, Nicholas and Felix | Hooks | |
| 2022 | Kathleen Lane | Timmy Dittrich & Karl Renney | Rich & Rose Denton | Steve Uhl | Team Taylor | Steve Uhl | Team Taylor | ||
| 2021 | Will Dailey | Tom Dailey | Anne Marije Veenland | Mike Lane & Renee Heffernan | Kim & Christina Pandapas | Kim Pandapas | Mike & Kathleen Lane | David & Mark Rubin | K&C Pandapas |
| 2020 | COVID | COVID | COVID | COVID | COVID | COVID | COVID | COVID | Cancelled – COVID |
| 2019 | Yati Harsono | Mike Lane | Stefan Thibideaux | Team Taylor | Hooks | Joe Fava | Team Martini | Erhardt Family | Matt Hooks / Rob Pascal |
| 2018 | Jim Taylor | Team Rubin | Jocelyn Cook | Pandapas | David Nelson | Peter Sorlien | Walter Colsman | Houget Family | Dave Nelson / Ken Delpapa |
| 2017 | Renee Heffernan | Matt Hooks | Bill Rothwell | Hourihan/Frisch | Ben Richardson | Elise Nash | Team Martini | Colsman Family | Richardson / Hufstader |
| 2016 | Elise Mazareas Nash | Larry Ehrhardt | Ann Souza | Pendleton/Raisides | Pendleton/Raisides | Christina Pandapas | Team Martini | Unawarded | Charley Pendleton / Jim Raisides |
| 2015 | David Martini | Matt Hooks | Larry Ehrhardt | Hourihan/Frisch | Jamie Holly | Jeff Shoreman | Steve Uhl | Unawarded | Jamie Holley |
| 2014 | Peter Frisch | Jamie Holley | Debbie Noble & Sarah Sheldon | Pendleton/Raisides | David Nelson | Kim Pandapas | Martinis | Raisides Family | Dave Nelson |
| 2013 | Linda Epstein | Dru Slattery | Breslin & Thorton | Pendleton/Raisides | Richardson | Doug Trees | Martinis | Zonnenberg Family | Richardson / Hufstader |
| 2012 | Chris Hufstader | Jim & Nat Taylor | Dru Slattery | Pendleton/Raisides | Pendleton/Raisides | Doug Trees | John Casler | Kaznoski Family | Charley Pendleton / Jim Raisides |
| 2011 | Elise Mazareas | Evan Cooke | Joe Fava | Pete Kaznoski & Evan Cooke | Pete Kaznoski & Evan Cooke | Charlie Pendleton | Hallawell/Beckett | Lane family | Evan Cooke / Pete Kaznoski |
| 2010 | Josh Wheeler | Peter Frisch | Tarin Comer | Kim & Christina Pandapas | Jim Raisides & Charlie Pendleton | Mike Lane | Hallawell/Beckett | Taylor family | Charley Pendleton / Jim Raisides |
| 2009 | Andrew Coffin | Jeff Shoreman & Dave Reynolds | Jennie Aspinal | Kim & Christina Pandapas | Jim Raisides & Charlie Pendleton | Steve Uhl | Jim Raisides / Charley Pendleton | ||
| 2008 | BJ Carpenter | Tom Despres | Jeff Shoreman & Dave Reynolds | Kim & Christina Pandapas | Jonathan Cressy | Maura Power | Jon Cressy / Doug Buell | ||
| 2007 | Jessica Berliner | Ian Peebles | Kim & Christina Pandapas | Jonathan Cressy | Bob Meyer | Jon Cressy / Charlie Pendleton | |||
| 2006 | Renee Heffernan | Doug Trees/Chris Small | Rick Berliner | Kim & Christina Pandapas | Kim & Christina Pandapas | Tom King | K&C Pandapas | ||
| 2005 | Tom King | Kim & Christina Pandapas | Kim & Christina Pandapas | K&C Pandapas | |||||
| 2004 | Miller Shropshire | Karl Renney / Pete Kaznoski | Andy Savage / Paul Zymba | Kim & Christina Pandapas | Kim & Christina Pandapas | John Casler | K&C Pandapas | ||
| 2003 | Marcel Nyffenegger | Nick Cann | Karl Renney | Kim & Christina Pandapas | Kim & Christina Pandapas | Kathleen & Michael Lane | K&C Pandapas | ||
| 2002 | Kimberly Pasley | John Thompson | Kim & Christina Pandapas | Jeremy & Katie Bloxham | Shan McAdoo | J&K Bloxham | |||
| 2001 | Renee Mitchell | Stephen Uhl | Kim & Christina Pandapas | Kim & Christina Pandapas | Christina Pandapas | K&C Pandapas | |||
| 2000 | Kate Dinsmore | Jeff Dinsmore | Stephen Uhl | Kim & Christina Pandapas | Trees / McAdoo | Peter Beckett | Trees/McAdoo | ||
| 1999 | Christine Fisher | Chris Adam | Beckett – Hallawell | Jonathan Cressy | Norm Cressy | Jonathan Cressy | |||
| 1998 | Shannon Lane | Shan McAdoo | Hallawell – Beckett | N. Cressy, H. Cressy, D. Buell | Kim Pandapas | Norm Cressy, H. Cressy, D. Buell | |||
| 1997 | Christina Pandapas | Joan Wheeler | Beckett – Hallawell | Norm Cressy, Doug Buell | David Graham | Norm Cressy, Doub Buell | |||
| 1996 | Elisabeth Casler | Jack Day | Hallawell – Beckett | Mike Lane / Rolfe Lofmark | BJ Mansfield / Mike Carpenter | Mike Lane/Rolfe Lofmark | |||
| 1995 | Mimi Ballou | Kent Hallawell | Kent Hallawell | Dimond, Hourihan, Steadman | BJ Mansfield / Mike Carpenter | Dimond, Hourihan, Steadman | |||
| 1994 | John Carullo | Fred Brehob | Fred Brehob | Bill and Renee Heffernan | Rolfe Lofmark | Bill and Renee Heffernan | |||
| 1993 | Tim McCaffrey | Mike Lane | R. Richmond & L. Brown | Brown/Richmond | Kent Hallawell | Brown/Richmond | |||
| 1992 | Rick Hamill | Jack Day | Mike Carpenter | Norman E. Cressy | Dan Duggan | Norman E. Cressy | |||
| 1991 | Joan Lane | Ken Adam / Mike Lane | K.Hallawell & D.Duggan | Lakin/Bolen/Fisher | Kevin Lane | Lakin/Bolen/Fisher | |||
| 1990 | Judy Adams | Bill Henze / Kevin Lane | Charles Loutrel | Jon Cressy | Margo Loutrel | Jon Cressy | |||
| 1989 | Keith Taylor | Eckart Colsman | Kent Hallawell | Larry Brown | Kent Hallawell | ||||
| 1988 | Ray Truche | Ken Adam | Bob Laken/Bruce Bolen | Krazy Kanguruh | Bob Kalin/Bruce Bolen | ||||
| 1987 | Mark Sullivan | Charlie Loutrel | Mike Carpenter | Charles T. Barr | Mike Carpenter | ||||
| 1986 | Cynthia Lewis | Mike Meehan / Mark Sullivan | Kent Hallawell | Joel Speare | Kent Hallawell | ||||
| 1985 | Susan Cohen | John Fisher / Bruce Bolen | Frank Hart | George Lail | Frank Hart | ||||
| 1984 | B.J. Mansfield | Mike Meehan | Eric Cressy | John Casler | Eric Cressy | ||||
| 1983 | Sharon Quayle | Larry Brown | Robbie Doyle | George Lail | Robbie Doyle | ||||
| 1982 | Neal Fine | James Bell | Norman E. Cressy | George Lail | Norman E. Cressy | ||||
| 1981 | Julie Nichols | Len Garfield / Sue Ogle | Mike Carpenter | John Casler | Mike Carpenter | ||||
| 1980 | Kay Parsons | John deBeer Jr / Stanley LaFond | Rob Hallawell | Kent Hallawell | Rob Hallawell | ||||
| 1979 | Sally McIntosh | Jim Beaton | Jim Taylor | John Casler | Jim Taylor | ||||
| 1978 | Maureen Graves | J.S. Casler | Fred Brehob | Fred Brehob | Fred Brehob | ||||
| 1977 | Elizabeth Dalquest | D.W. Altman / J.H. Taylor | Peter DeWolfe | Len Dalquest | Peter DeWolfe | ||||
| 1976 | Chris Howes | M.G. Fusillo | Norman E. Cressy | Dick Welch | Norman E. Cressy | ||||
| 1975 | Joanne Bowman | C.E. Mara | Peter DeWolfe | Sarah Silverstein | Peter DeWolfe | ||||
| 1974 | Debra DeWolfe | D.C. Berkey | Norman E. Cressy | Millard & David Tucker /Declan Murphy | Norman E. Cressy | ||||
| 1973 | Sid Kimber | S.T. Kimber | Fred Brehob | Dick Welch | Fred Brehob | ||||
| 1972 | R.P. Whitman | Fred Brehob | Greta & R.C. Triplett | Fred Brehob | |||||
| 1971 | J.W. Brown | Fred Brehob | Joanne Bowman | Fred Brehob | |||||
| 1970 | M.N. Tucker | Fred Brehob | Peter Branch | Fred Brehob | |||||
| 1969 | W.R. Creamer / D.F. Allen Jr. | D.F. Allen, Jr.W.R. Creamer | John A. MacDonald, Jr. / Peter DeWolfe | W.R. Creamer / D.F. Allen, Jr. | |||||
| 1968 | J. Kenneth Baxter, Jr. | William K. Henze | J. Kenneth Baxter, Jr. | ||||||
| 1967 | J. Kenneth Baxter, Jr. | John E. Burke | J. Kenneth Baxter, Jr. | ||||||
| 1966 | J. Kenneth Baxter, Jr. | Frederick Schmid | J. Kenneth Baxter, Jr. | ||||||
| 1965 | J. Kenneth Baxter, Jr. | ||||||||
| 1964 | J. Kenneth Baxter, Jr. |
Trophies
Richie Santos Trophy
Outstanding Crew, awarded at annual banquet.
Perpetual, silver cup on a wooden base, engraved with winners & years won. Donated by John Burke.
Named in memory of John Burke’s crew, Richie Santos. This trophy is awarded each season to that individual who most distinguishes him or herself in a crew capacity. Candidates must be nominated by a skipper registered in the fleet, and nominations typically are submitted in a letter to the fleet president. Final selection is at the discretion of the president, and can be judged on the basis of long-term contribution, overall performance during a single season or regatta, or even on a single compelling or outstanding event.
Most Improved Award
Most improved skipper, awarded at annual banquet.
Perpetual Pitcher – Purchased by fleet in early 1970s – Dick Welch president.
Awarded each year to the skipper who demonstrates the most improvement from the previous season. Selection is based primarily on a comparison of the overall score for all local events, including the EYC Spring Series, MRA series, Twilight series, Race Week, Independence Day regatta, Labor Day regatta, and the CYC Fall series. Typically, boats demonstrating comparable improvement higher in the ranking win over those who improve lower in the ranking.
Rookie of The Year
Best new skipper, awarded at annual banquet.
Brass fog horn, with names of winners and years won.
Awarded to that first-year skipper with the most impressive showing, typically based on overall scores. However, this trophy also has been awarded to late comers on the basis of an outstanding showing in the Fall Series.
Nick Nichols Trophy
Best Overall (the whole enchilada), awarded at annual banquet.
Cup or plaque
Named in memory of long-time Townie and Rhodes skipper Nathan ‘Nick’ Nichols, this trophy is awarded to the boat with the lowest overall point total in all local events, including the EYC Spring Series, all regular MRA series, Twilight series, Race Week, Independence Day regatta, Labor Day regatta, and the CYC Fall series.
Charlie Barr Trophy
Winner of Twilight Series, awarded at annual banquet.
Named in memory of long-time Rhodes racer Charlie Barr, this trophy is presented to the boat with the lowest overall point total for the Thursday evening Twilight Series.
President’s Trophy
Greatest contribution to the fleet, awarded at annual banquet.
Perpetual, silver pitcher, engraved with winners & years won.
Awarded each year to a person or persons who make the most outstanding contribution to the fleet that year. Final selection is at the sole discretion of the president.
The Marblehead Fleet #5 Race Week Trophy (also called “the Spittoon”)
Best Fleet #5 boat in Marblehead Race Week, awarded at Race Week.
Perpetual, brass spittoon, engraved with winners & years won.
Awarded each year to the skipper of the Fleet #5 boat with the best finish in Race Week.
Joel Spear Glass
Winner of Twilight Race, held for pickup by weekly winners at CYC front desk.
Glass – emblazoned with class logo and Joel’s name.
Named in memory of long-time Rhodes racer and Race Committee member Joel Spear, these glasses are presented to the 1st place boat for each evening of the Thursday Twilight Series.