| May 12 | Soup Kitchen |
| May 22 | The Year of Magical Thinking & Nora, Hedda, & Ellida do 4:48 Psychosis |
| May 25 | Great Northwest Stage Combat Extravaganza |
| May 27 | Introduction to Spinning |
| May 28 | Jefferson County Soccer Fall Registration |
| June 01 | Adults - Learn to Sail |
| June 04 | WordPlay Reading - 'Orpheus Descending' by Tennessee Williams |
| June 04 | Weekly Thursday Night Social Dance |
| June 04 | Taste of Port Townsend |
| June 05 | First Friday Lecture, Hiking on the Olympic Peninsula |
| June 05 | Castle Key Live Jazz |
| June 05 | On the Dock of the Bay Concert |
| June 05 | Burnin' Mountain |
| June 05 | Port Ludlow Friday Market |
| June 05 | W.S.U. Master Gardners Friday Plant Clinic |
| June 06 | 26th Classic Mariners' Regatta |
| June 06 | Port Townsend Gallery Walk |
| June 06 | Castle Key Live Jazz |
| June 06 | Native American Basket Weaving Demonstration |
| June 06 | Port Townsend Farmers Market |
| June 06 | Historic Downtown Walking Tour |
| June 06 | PT SHORTS: The Story Girl |
| June 06 | 'Swoon' Under the Full Moon in June |
| June 06 | PT Songlines Choir presents a SONGFEST and interactive concert to benefit Key City Public Theatre |
| June 06 | Trillium: Songs of Hope and Inspiration |
| June 06 | Hood Canal Bridge Opening Bash |
| June 06 | Nature Walk in the Quimper Wildlife Corridor: A Walk on Tibbal's Plateau and Cappy's Trails |
| June 06 | Zingara |
| June 06 | ReCyclery Rummage Sale and Salmon Dinner |
| June 06 | Port Townsend Schooner Co. Open House |
| June 06 | Pacific NW National Scenic Trail Work Party |
| June 07 | Historic Uptown Walking Tour |
| June 07 | SoulFull Sunday Dance Jam |
| June 07 | Free P.T. ReCyclery Bike Repair Clinic |
| June 07 | Chimacum Farmers' Market at the Grange |
| June 07 | 30th Annual Port Townsend Chili Cook-off |
| June 11 | Weekly Thursday Night Social Dance |
| June 11 | Northwind Reading Series |
| June 11 | Folk, Blues and Favorites with Brian Ellard |
| June 12 | Potters Council Handbuilding & Paperclay, Ceramic Workshop |
| June 12 | Castle Key Live Jazz |
| June 12 | Olympic Sound Collective |
| June 12 | Port Ludlow Friday Market |
| June 12 | W.S.U. Master Gardners Friday Plant Clinic |
| June 12 | Lincoln Crockett, Chris Kokesh & Port Townsend's Southbound |
| June 13 | Adults - Learn to Sail |
| June 13 | Castle Key Live Jazz |
| June 13 | Taming the Sugar Beast class with Heidi Snyder, Certified Nutrition Consultant |
| June 13 | Port Townsend Farmers Market |
| June 13 | Historic Downtown Walking Tour |
| June 13 | Ari Joshua & Friends |
| June 13 | ACTING WORKSHOP: Acting and the Word, approaching Shakespeare's text with Paula Bennett |
| June 13 | Terry West Saturday Dance |
| June 13 | Northwest Blues Stars: The Surf Monkeys |
| June 14 | Historic Uptown Walking Tour |
| June 14 | SoulFull Sunday Dance Jam |
| June 14 | Chimacum Farmers' Market at the Grange |
| June 14 | Salsa Dance Night |
| June 14 | Art Opening, Artist Andrea Lawson |
| June 15 | Adults - Learn to Sail |
| June 15 | Open Mic |
| June 18 | Food and Farm Camp |
| June 18 | Draft Horse Logging - Greg Lange (Free Admission) |
| June 18 | Live Jazz featuring Joe Baque and Friends |
| June 19 | Castle Key Live Jazz |
| June 19 | The O'Meara Dance Studio Presents... |
| June 19 | Professor Gall |
| June 19 | Port Ludlow Friday Market |
| June 19 | W.S.U. Master Gardners Friday Plant Clinic |
| June 19 | Blues, Rock, Roots Legend Geoff Muldaur |
| June 19 | Wild Rose Chorale Summer A Cappella Concert |
| June 19 | Wine Tasting: Zinfandels |
| June 20 | Secret Garden Tour |
| June 20 | Castle Key Live Jazz |
| June 20 | Harp & Voice Concert |
| June 20 | Port Townsend Farmers Market |
| June 20 | Historic Downtown Walking Tour |
| June 20 | Summer Solstice Pottery Sale |
| June 20 | The Paul Benoit Band |
| June 20 | BOOM! Fest |
| June 20 | Randy Oxford Blues Band |
| June 20 | Among Friends: Launch Celebration |
| June 20 | Artists' Studio Sale At Greybird Barn |
| June 20 | Summer Sailstice Charters |
| June 21 | Young Artists Project: Summer High School Arts Camp |
| June 21 | Lisa Lanza in Concert at the Rose Theatre |
| June 21 | Historic Uptown Walking Tour |
| June 21 | SoulFull Sunday Dance Jam |
| June 21 | Chimacum Farmers' Market at the Grange |
| June 21 | Father's Day Sail aboard Adventuress |
| June 21 | Father's Day Afternoon Sail aboard Adventuress |
| June 21 | Celebrating the Embodied Voice - A Sound and Movement Feast for the New Year |
| June 21 | Chuck Easton Recitals & Penultimate Sunday Jazz Jam |
| June 21 | Wild Rose Chorale Summer A Cappella Concert |
| June 21 | Body and Earth: An Outdoor Dance Experience |
| June 22 | Open Mic |
| June 23 | Dances of Universal Peace |
| June 25 | Weekly Thursday Night Workshop and Dance - Final Night |
| June 25 | Sailing aboard Pleiades on Port Townsend Bay |
| June 25 | Candlelight Concert |
| June 25 | Townsend Live with Andre Feriante and Eric Fridrich |
| June 25 | Pandit Shivnath Mishra and Deobrat Mishra |
| June 26 | Centrum presents the Borromeo String Quartet |
| June 26 | Castle Key Live Jazz |
| June 26 | Play: What the Butler Saw |
| June 26 | The Jake Shaw Trio |
| June 26 | Port Ludlow Friday Market |
| June 26 | W.S.U. Master Gardners Friday Plant Clinic |
| June 26 | Jump Blues with The Insomniacs |
| June 26 | Kirtan with Deobrat Mishra |
| June 26 | Waging Peace, Designing Justice Performance |
| June 26 | Body Prayer - A Soul Motion Experience! 3-Day Workshop with Zuza Engler |
| June 26 | Skidder Hill |
| June 26 | The Dwyer Family |
| June 27 | Centrum presents the Borromeo String Quartet |
| June 27 | Olympic Music Festival |
| June 27 | Vaudeville Extravaganza with the New Old Time Chautauqua |
| June 27 | Adults - Learn to Sail |
| June 27 | Castle Key Live Jazz |
| June 27 | Port Townsend Farmers Market |
| June 27 | Rakers Car Club Summer 2009 Car Show |
| June 27 | Historic Downtown Walking Tour |
| June 27 | Zydeco Cajun Dance |
| June 27 | Diggabone |
| June 27 | Cheese Making Class |
| June 27 | Fort Flagler Outdoor Concert |
| June 27 | PT Elks Lodge Western Nite |
| June 27 | The Mark Dufresne Blues Band |
| June 27 | The Billy Winters Band |
| June 27 | County Wide Open House - over 227 Homes on Tour |
| June 27 | Vienna Teng in Concert - Solo Performance |
| June 28 | Festival of American Fiddle Tunes |
| June 28 | Port Townsend Summer Band Concert |
| June 28 | Historic Uptown Walking Tour |
| June 28 | SoulFull Sunday Dance Jam |
| June 28 | Chimacum Farmers' Market at the Grange |
| June 28 | Special SoulFull Sunday Dance with Zuza Engler:Body Prayer |
| June 28 | Slow Food Cheese Tasting |
| June 28 | Folk, Blues and Rock with Brian Ellard and Friends |
| June 29 | Youth - Learn to Sail (ages 5-7) |
| June 29 | Youth - Learn to Sail |
| June 29 | Adults - Learn to Sail |
| June 29 | Port Townsend Chamber Meeting: State Rep. Lynn Kessler |
| June 29 | Live Music and Word Open Mic |
| June 30 | West Camp for Girls |