As stated in the about section, Skip likes community theater.
He was deeply involved with The Wilton Playshop for 0ver 30 years where he's served as Executive Producer, Historian, and President in the past. He now directs in local community and youth theater groups. He has directed in Westport, New Canaan, Stratford, Danbury, and Wilton.
His directing credentials include;
- Death Trap! (Wilton Playshop as Assistant Director 1994)
- Arsenic and Old Lace (Wilton Playshop 1995)
- Guys and Dolls (Wilton Student Summer Playshop 1995)
- How to Succeed in Business Without Really Trying (Wilton Student Summer Playshop 1998)
- 1776 (Wilton Playshop 2001)
- My Big Fat Italian Feast (For The Wilton Singers, he wrote it as well 2002)
- Wasp on this Island (For The Wilton Singers, which he also wrote 2003)
- Camping with Henry and Tom (A play reading at The Wilton Playshop 2004)
- Wenceslas Square (Wilton High School Underclassman Play 2005)
- The Foreigner (Westport Community Theater 2005)
- Six by Six (Wilton Playshop Student Summer Playshop 2006. Six David Ives pieces directed by six student directors)
- Candida (Town Players of New Canaan)
- The Nerd (Wilton Playshop 2007)
- High School Musical (Wilton Children's Theater 2007)
- Grease (Wilton Children's Theater Summerstage 2008)
- Willy Wonka (Wilton Children's Theater 2008)
- The Hound of the Baskervilles (Westport Community Theater 2010)
- Annie (Wilton Children's Theater 2009)
- Camelnot/Twisted Fairytales (Wilton Children's Theater Summerstage Jr. Debut Production 2009)
- Bye Bye Birdie (Wilton Children's Theater 2010)
- Jungle Book Jr. (Wilton Children's Theater Summerstage Jr. 2010)
- Mr. Smith and the Preamble (Startford Arts Festival 2010)
- Mulan Jr. (Wilton Children's Theater 2011)
- 101 Dalmatians (Wilton Children's Theater Summerstage Jr. 2012)
- Beauty and the Beast Jr. (Wilton Children's Theater 2012)
- Disney's Little Mermaid (Wilton Children's Theater 2013)
- Aladdin Jr. (Wilton Children's Theater Summerstage Jr.2013)
- Shrek! The Musical (Wilton Children's Theater 2013)
- Camp Rock! (Wilton Children's Theater 2014)
- Annie Kids (Wilton Children's Theater Summerstage Jr.2015)
- Relative Values (Wilton Playshop 2015)
- The Wizard Of Oz (Wilton Children's Theater 2015)
- The Aristocats Kids (Wilton Children's Theater Summerstage Jr. 2016)
- High School Musical (Wilton Children's Theater 2016)
- How to Succeed in Business Without Really Trying (Wilton Playshop 2017)
- Onstage Blog Nominated /Awarded 2017
- Best Choreography: Judy Abbatiello
- Outstanding Ensemble in a Musical
- Outstanding Director of a Musical: Skip Ploss
- Outstanding Actress in a Featured Role in a Musical: Lisa Dahlstrom
- Outstanding Actor in a Leading Role in a Musical: Jackson Gallati
- Outstanding Actress in a Leading Role in a Musical: Nikki Scamuffo
- Outstanding Musical
- Aladdin Kids (Wilton Children's Theater Summerstage Jr. 2017)
- Willy Wonka (Wilton Children's Theater 2017)
- The Lion King Kids (Wilton Children's Theater Summerstage Jr. 2018)
- Annie (Wilton Children's Theater 2018)
- 101 Dalmatians (Wilton Children's Theater Summerstage Jr. 2019)
- Disney's The Lion King (Wilton Children's Theater 2019)
- The Aristocats Kids (Wilton Children's Theater Summerstage Jr. Remote Edition 2020)
- WCT TV (Wilton Children's Theater 2020 a video magazine formatted talent show)
- Shrek Jr. (Wilton Children's Theater 2021)
- Seussical Kids (Wilton Children's Theater Summerstage Jr. 2022)
- Madagascar Jr. (Wilton Children's Theater 2022)
- Godspell (2012) (Wilton Playshop 2023)
- The Addams Family (Musicals at Richter 2023)
- Review: Broadway World
- Review: Newtown Bee
- Review: Danbury Patch
- Review: Brewster Hamlet Hub
- Broadway World Award Nominations (non-professional)
- Best Musical
- Best Direction of a musical: Skip Ploss
- Best Enemble
- Best Musical Direction: Andrew Gadwah
- Best Choreography: Lindsay Miller
- Best Performance in:
- Jacob Rogotzke (Gomez)
- Arianna Straznick (Morticia)
- Best Supporting Performer in:
- Ted Schwartz (Uncle Fester)
- Madison Beilmeier (Wednesday)
- Jen MacNeil Dannenberg (Grandma)
- Denise Milmerstadt (Alice)
- Disney's The Junglebook Kids (Wilton Children's Theater's Summestage Jr. 2023)
- Elf Jr (Wilton Children's Theater. Fall 2023)
- Finding Nemo Kids (Wilton Children's Theater Summer Stage Jr. Summer 2024)
- Flags (Broadway Bound Theatre Festival at Town Players of New Canaan Summer 2024) in preproduction
- Singing In The Rain (Wilton Children's Theater Fall 2024 ) in preproduction
- Into The Woods (Wilton Playshop Spring of 2025 ) in preproduction
Set designs include;
- Arsenic and Old Lace
- 1776
- The Perfect Party
- Deathtrap
- The Secret Garden
- The Sweet Bye N Bye
- Wenceslas Square
- High School Musical
- Candida
- Camelot
- Big River
- Guys and Dolls
- How to Succeed in Business Without Really Trying
- Relative Values (with Gini Fisher)
- Commons of Pensacola
- Godpsell 2012 (with Gini Fisher)
- The Addams Family
- Grease
- Flags
For more information on Children's Theater programs including Summerstage Jr go to the organization's website at http://www.wiltonchildrenstheater.org.
For more information on The Wilton Playshop, visit their website at www.wiltonplayshop.org
For more information on Musicals at Richter, visit their website at www.musicalsatrichter.org
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