| Date | Event |
| 5-1 thru 31 | Rhododendron Festival - Port Townsend |
| 5-17,18 | Waterfront Festival - Anacortes |
| 5-17,18 | 43rd Penn Cove Canoe & Water Festival - Coupeville |
| 5-18 | Rhody Run XXVIII - Port Townsend |
| 5-22 thru 24 | Trawler Festival - Anacortes |
| 5-24 | Memorial Day Parade - Coupeville |
| 5-25 | AAUW Kitchen Tour - starts in Coupeville Rec Hall |
| 6-7 | Arts and Antique Walk - Coupeville |
| 6-14 | Father’s Day Weekend Car Show - Greenbank Farm |
| 6-21 | Summer Solstice Barn Dance - Concerts on the Cove - Coupeville |
| 6-21 | Beachcombers Bazaar Largest Garage Sale - Oak Harbor |
| 6-21,22 | Horse Lover’s Art Show & Benefit - Coupeville |
| 6-27 thru 29 | Greenbank Artist Show and Sale |
| 6-28,29 | 29th World’s Largest Lion’s Club garage sale - Coupeville |
| 6-28,29 | 1st Annual Wharf Festival - Coupeville |
| 6-29 thru 7-6 | Festival of American Fiddle Tunes - Port Townsend |
| 7-3,4 | Fireworks everywhere on Whidbey & on Penn Cove |
| 7-4 | 4th of July Parade - Oak Harbor |
| 7-4 | Maxwelton’s 4th of July Parade - Clinton |
| 7-4 | July 4th Celebration - Anacortes |
| 7-12 | Bayview Nights Car Show - Bayview Corner Oak Harbor |
| 7-12,13 | 5th Annual Spirit of NW Art show & Benefit - Coupeville |
| 7-12,13 | Choochokam Art festival - Langley |
| 7-13 | Southern Cross - Concerts on the Cove - Coupeville |
| 7-19 | Annual Very Berry Festival - Coupeville |
| 7-20 | Car Show - Anacortes |
| 7-20 thru 25 | Race Week’s annual yaught sailing contests - Penn Cove |
| 7-25 thru 27 | 53nd Annual Barbershop Show and Salmon BBQ - Anacortes |
| 7-25,26 | Ragnar Relay Northwest Passage 877-837-3529 |
| 7-26,27 | Loganberry Festival - Greenbank Farm |
| 7-27 thru 8-3 | Country Blues Festival - Port Townsend |
| 8-1 | Greta Matassa - Concerts on the Cove - Coupeville |
| 8-1 thru 3 | Anacortes Arts Festival |
| 8-2 | 8th annual Meerkerk Medley - Meerkerk Gardens |
| 8-2 | Whidbey Island Triathlon - S. Whidbey Parks & Rec |
| 8-2,3 | Lavender and Wind Farm Festival - Coupeville |
| 8-6 thru 9 | Skagit County Fair |
| 8-8 | Wine Tasting and Juried Gallery Preview - Coupeville |
| 8-9,10 | 44th annual Arts and Crafts Fair - Coupeville |
| 8-9 | Whidbey Island’s Scottish Highland Games - Greenbank Farm |
| 8-14 thru 17 | Island County Fair - Langley |
| 8-16 | Fast Machine - Concerts on the Cove - Coupeville |
| 8-23,24 | 1st annual Summer Art Studio Tour - Coupeville |
| 8-23 thru 9-7 | 5th Whidbey Woodpalooza Wood show - Coupeville |
| 8-30 thru 9-1 | 5th Annual Jazz Festival - Anacortes |
| 9-4 | Plein Air Painters U.S. Open - Coupeville |
| 9-5 thru 7 | Wooden Boat Festival - Port Townsend |
| 9-5 thru 7 | Volksmarch - Walking Festival |
| 9-6 | Art and Antique walk - Coupeville |
| 9-6 | Military Appreciation Picnic - www.OakHarborChamber.com |
| 9-7 | Annual Wag & Walk www.waifanimals.org |
| 9-8 | Yacht Club boat show - Oak Harbor |
| 9-13 | 12th Annual Antique Engine & Machinery Show - Anacortes |
| 9-13 | Soap box Derby - Langley |
| 9-14 | An-O-Chords - Concerts on the Cove - Coupeville |
| 9-19 thru 23 | Django Fest NW at WICA - 360-221-8262 |
| 9-20 | Fidalgo Bay Day - Anacortes |
| 9-27 | 100/50 mile Cycling Tour d’ Whidbey - Coupeville |
| 9-27,28 | Fort Casey 11th annual kite flying contest |
| 9-28 | Motorcycle "Oyster Run" - Anacortes |
| 10-3 thru 5 | 2nd Annual Whidbey Island Farm Tour - all Whidbey Is. |
| 10-6 thru 15 | 6th Annual Coupeville Scarecrow Corridor |
| 10-11 | Oktoberfest - Greenbank Farm |
| 10-11 | Pumpkin Festival - Coupeville |
| 10-11,12 | Uniquely Whidbey Trade Fair - Coupeville |
| 10-11 | Autumn Rhodie sale - Meerkerk Gardens |
| 10-25 | Apple Day and Mutt Strut dog parade - Oak Harbor |
| 11-2 | 2nd Annual B&B Open House Tour - Coupeville & Greenbank |
| 11-7,8 | 30th Anniv - founding of Ebey’s Landing Nat Historic Reserve - Coupeville |
| 11-7,8 | Whidbey Weaver’s Guild Show - Greenbank Farm |
| 11-21 | Tree Lighting Celebration - Greenbank Farm |
| 11-29 | Lighting of Langley - 360-221-6765 |
| 12-5 | Annual Lions Club Parade & Tree Lighting - Anacortes |
| 12-6 | Christmas in Coupeville - with evening parade and more |
| 12-6 | Arts and Crafts Walk - Coupeville |
| 12-14,15 | Whidbey B&B Tour and Tastes #1 - 360-221-6765 |
| 12-21,22 | Whidbey B&B Tour and Tastes #2 - 360-221-6765 |
