| March 19 | Adult Pickleball |
| April 30 | Play: Birnham Woods |
| May 01 | Art Wave - Childrens' Art in the Stores |
| May 01 | First Friday Lecture, Historical Preservation Awards |
| May 01 | Sea Marine Opening Day |
| May 01 | Castle Key Live Jazz |
| May 01 | Deadwood Revival CD Release Party |
| May 01 | Cafe Combo: Live Jazz, Pop, and Blues |
| May 01 | Wine Tasting |
| May 01 | CHICAGO: Port Townsend High School |
| May 02 | JeffCo HomeShow |
| May 02 | Port Townsend Gallery Walk |
| May 02 | Natural Foods Class |
| May 02 | Roy Rogers and The Delta Rhythm Kings |
| May 02 | 'Talking Heads' Local Documentary Screening and Discussion |
| May 02 | Model Boat Building Workshop |
| May 02 | Castle Key Live Jazz |
| May 02 | Third Annual Chair Affair Gallery Walk Night |
| May 02 | Natural Foods Class: Nutrients, Functional Foods & Food Supplements, Diet Choices and Food Allergies |
| May 02 | Artist Reception for Patricia Taynton |
| May 02 | PT Shorts: Letters Of The 20th Century - Letters written by famous and not so famous people |
| May 02 | Extended Earth Day at Fort Flagler |
| May 02 | Nature Walk in the Quimper Wildlife Corridor |
| May 02 | Zydeco & Cajun Dance |
| May 02 | Olympic Mountains Photo Exhibit Opens |
| May 02 | Astronomy Day |
| May 02 | Mandolin Workshop |
| May 02 | Port Townsend Farmers Market Opening Day |
| May 03 | Vocal Performance Workshop with Judith-Kate Friedman |
| May 03 | Chimacum Farmers' Market at the Grange |
| May 04 | Monday Night Live Open Mic |
| May 06 | Heartsaver First Aid - CPR Class |
| May 06 | Traditional Sock Knitting Class |
| May 06 | Big Band Night |
| May 06 | Free Craft Workshops |
| May 07 | Holding Your Gaze: The Literature of Witness |
| May 07 | Clemente Course: Free Lecture Series |
| May 07 | Business Expo |
| May 07 | Comedy Night: An evening of stand-up with Gabriel Rutledge and friends |
| May 07 | Andy Macie Music Foundation Fundraiser |
| May 08 | Chamber Music Society of Port Townsend Presents |
| May 08 | Castle Key Live Jazz |
| May 08 | Badd Dog Blues Society |
| May 08 | Poetic Justice Theatre Ensemble |
| May 08 | Dwyer Family Band |
| May 08 | Port Ludlow Friday Market |
| May 09 | Opening Day on Port Townsend Bay |
| May 09 | Rhododendron Arts & Crafts Fair |
| May 09 | Natural Foods Class |
| May 09 | 'Talking Heads' Local Documentary Screening and Discussion |
| May 09 | Second Nature by John Witte |
| May 09 | Contra Dance with Warren Argo & Contradictions |
| May 09 | Castle Key Live Jazz |
| May 09 | Natural Foods Class: Diet Choices and Food Allergies |
| May 09 | Opening Boating Day Parade |
| May 09 | Schooner Alcyone, Opening Day-Open House |
| May 09 | The Humbuckers |
| May 09 | Badd Dog Blues Society |
| May 09 | Bonzo The Clown & The Peregrine Public Theatre |
| May 09 | Paul Green and Straightshot Blues Band |
| May 09 | Port Townsend Farmers Market |
| May 09 | Post Office Food Drive |
| May 09 | Contra Dance |
| May 09 | On The Upswing of Art, A New Chapter |
| May 09 | Second Nature: poet John Witte |
| May 09 | Ezekiel Kelly |
| May 09 | Rig Your Boat Workshop |
| May 10 | Salsa Night |
| May 10 | Mother's Day Tea & Fashion Show - Cancelled! |
| May 10 | Jim Nyby |
| May 10 | Mother's Day Family Concert |
| May 11 | Rhododendron Festival Rhododendron Dedication |
| May 11 | 74th Annual Rhododendron Festival |
| May 11 | Monday Night Live Open Mic |
| May 12 | Clemente Course: Free Lecture Series |
| May 12 | Soup Kitchen |
| May 13 | Life and Times of Judge James Swan |
| May 13 | Tom Waits Tribute Night |
| May 13 | Rhody Festival Trike Race |
| May 14 | Rhododendron Festival Carnival |
| May 14 | WordPlay Reading - 'Harvey' by Mary Chase |
| May 14 | Removing the Stain of Guantanamo |
| May 14 | Northwind Reading Series - Sandy Diamond and Erin Fristad |
| May 14 | Rhododendron Festival Pet Parade |
| May 15 | Rhododendron Festival Kiddies Parade |
| May 15 | 'Talking Heads' Local Documentary Screening and Discussion |
| May 15 | Castle Key Live Jazz |
| May 15 | Rock the Rhody |
| May 15 | Blues with John Skooch Cugno and his Delta 88's |
| May 15 | Wine Tasting |
| May 15 | Franco Bertucci |
| May 15 | Rhody Festival Past Royalty Reunion |
| May 15 | Port Ludlow Friday Market |
| May 16 | Jitterbug Swing Dance |
| May 16 | Rhododendron Festival Grand Parade |
| May 16 | Rock Show at the Legion Hall |
| May 16 | Castle Key Live Jazz |
| May 16 | Eric Miller Show |
| May 16 | The Seth Walker Band |
| May 16 | Dwyer Family Band |
| May 16 | Larry Scott Trail Work Party |
| May 16 | Rhody Rendezvous! |
| May 17 | 31st Annual Rhody Run |
| May 17 | Benefit Concert for the Animals |
| May 17 | Strangefeather (young San Francisco rock band) |
| May 17 | Jim Nyby |
| May 19 | The Food Co-op Annual General Meeting |
| May 19 | Candlelight Concert |
| May 21 | Global Heat Music and Dance Ensemble |
| May 21 | Jim Scott in Concert |
| May 21 | Free Lecture: Carving Totem Poles |
| May 21 | The Pilgrims Way: A Night of Story, Song, and Farewells |
| May 21 | Northwind Reading Series Adrianne Harun and Elea Carey |
| May 21 | Weekly Thursday Night Workshop and Practice Dance |
| May 22 | Fort Worden Children's Choir Festival & Concert |
| May 22 | David Jacob-Strain |
| May 22 | Dwyer Family Band |
| May 22 | Skidder Hill |
| May 22 | The Year of Magical Thinking & Nora, Hedda, & Ellida do 4:48 Psychosis |
| May 22 | Cort Armstrong Band |
| May 22 | Port Ludlow Friday Market |
| May 23 | Olympic Art Festival |
| May 23 | ShrimpFest |
| May 23 | Victorian Language of Flowers Workshop |
| May 23 | Castle Key Live Jazz |
| May 23 | Natural Foods Class: Medicinal Uses of Everyday Foods |
| May 23 | Historic Downtown Walking Tour |
| May 23 | Alice Stuart & The Formerlys |
| May 23 | Port Townsend Farmers Market |
| May 23 | Silent Art Auction |
| May 23 | David Michael & Dari in Concert |
| May 23 | One Performance Only: The Magic Chamber, 30 Seats, 60 Minutes, One Outrageous Event |
| May 23 | A Branch from the Lightning Tree: an evening with Martin Shaw |
| May 23 | Deer Run 09 |
| May 23 | Colin Lake & Wellbottom |
| May 24 | Historic Uptown Walking Tour |
| May 24 | Alice Stuart & The Formerlys - May 23 only! |
| May 24 | Penultimate Sunday Jazz Jam |
| May 24 | Jim Nyby |
| May 24 | The Wyrd and the Wyld: a workshop with Martin Shaw and Daniel Deardorff |
| May 24 | SoulFull Sunday Dance Jam |
| May 25 | Great Northwest Stage Combat Extravaganza |
| May 25 | Memorial Day Concert |
| May 26 | Dances of Universal Peace |
| May 27 | Introduction to Spinning |
| May 28 | Kolvane Blues Band |
| May 28 | Towns End - Live |
| May 28 | Weekly Thursday Night Workshop and Practice Dance |
| May 28 | Miho & Diego Duo with Matt Sircely |
| May 28 | Jefferson County Soccer Fall Registration |
| May 29 | Castle Key Live Jazz |
| May 29 | Jim Nyby and The F Street Blues Band |
| May 29 | Concert to Benefit Ugandan AIDS Orphans |
| May 29 | Ezekiel Kelly |
| May 29 | The Improvathon: 24 hours of Improvisation Just For The Love Of It. |
| May 29 | Lucky Brown & the Funk Revolution |
| May 29 | Grand Opening - Better Living Through Coffee |
| May 29 | Port Ludlow Friday Market |
| May 29 | Candlelight Concert |
| May 29 | W.S.U. Master Gardners Friday Plant Clinic |
| May 30 | Castle Key Live Jazz |
| May 30 | Taming the Sugar Beast class with Heidi Snyder, Certified Nutrition Consultant |
| May 30 | Historic Downtown Walking Tour |
| May 30 | Port Townsend Farmers Market |
| May 30 | Dwyer Family Band |
| May 30 | Shamanic Cheerleading Playday |
| May 30 | BIG Yoga with Terry Wagner |
| May 30 | Chuckanut Drive & Big Sur |
| May 30 | Port Townsend Pirouettes Synchronized Swimming Show |
| May 31 | Historic Uptown Walking Tour |
| May 31 | Jim Nyby |
| May 31 | SoulFull Sunday Dance Jam |
| May 31 | Benefit Comedy Show for Jay Sierra |
| May 31 | Chimacum Farmers' Market at the Grange |