Windmill Weekend 2009 Winners
CHOWDER CONTEST
| 1st Place | Aidan's (located at Willy's) | #5 |
| 2nd Place | Jimmy D's | #1 |
| 3rd Place | Elks Lodge | #3 |
SAND ART
| Best of Show | Stanfa/Ponichtera - "Enrapture of the Sea" | |
| Viewer's Choice | Brian-Owen-Kate, "Guess Who's Coming to Dinner?" | |
| Family Group | 1st Place | Winch Family, "Rock Harbor" |
| 2nd Place | Schmidt Family, "Save Our Sea Turtles" | |
| 3rd Place | Nobili Family, "The Sea" | |
| 4th Place | The Mumfords, "The Lobster Family" | |
| 5th Place | Senorita PP & the Pips, "Tickle My Claw" | |
| Youth Category | 1st Place | Jimmy K, "Penniman House" |
| 2nd Place | Sarah and Shaun, "Mermaids" | |
| 3rd Place | Bryce W., "The Naviator" | |
| Teens, Adults, Adult-Child Pair | 1st Place | Erika & Barb, "The Lighthouse of Alexandria" |
| 2nd Place | Michael Willett, "Shark" | |
| 3rd Place | Adam & Nick, "Shipwreck" | |
PARADE
| Commercial Entry | 1st Place | Nickerson Service Garage |
| 2nd Place | Arnolds | |
| 3rd Place | Orleans-Eastham Elks | |
| Organization and Group Entries | 1st Place | Eastham Elementary School |
| 2nd Place | EFFI's | |
| 3rd Place | Eastham Historical Society | |
| 4th Place | Eastham Employees and Library | |
| 5th Place | Adult Day Care |
ROAD RACE
| 5 Mile Race | ||
| First Overall Male | Tony Ryba | |
| Second Overall Male | Jay Kolodzinski | |
| Third Overall Male | Bruce Hurley | |
| First Overall Female | Moira Nobili | |
| Second Overall Female | Dawn Varnum | |
| Third Overall Female | Ali Winslow | |
| 2 Mile Race | ||
| First Overall Male | Brandon Bausch | |
| Second Overall Male | Eddie Wilcox | |
| Third Overall Male | Sam Poole | |
| First Overall Female | Katie McCully | |
| Second Overall Female | Robyn Argo | |
| Third Overall Female | Julia Smith | |