Scroll down to see my:
Most shows are free and all ages (usually until 9pm) unless stated otherwise below.
See you there!
*Playing with Band
May 2025
May 1 Thurs | 5-7pm | Park & Main (Carlton)
May 2 Fri | 6-8pm | Kopitos Restaurant (Newberg)
May 3 Sat | 5-7pm | West Hills Vineyards (Salem)
May 4 Sun | 2-4pm | Benedetto Vineyards* (Dallas)
May 5 Mon | 6:30-7:30pm | Shades of Brew Brewery (S. Salem)
May 8 Thurs | 10:30-11:45am | Private Event* (Unitus Event)
May 9 Fri | 2-3pm | Private Event (Keizer)
May 10 Sat | All Day | Private Event* (Lorely Birthday)
May 16 Fri | 4-7pm | Van Duzer Vineyards (Wine Club Only)
May 17 Sat | 2-5pm | Cubanisimo Vineyards (Salem)
May 18 Sun | 10am-12pm | Gilgamesh: The River (Independence)
May 18 Sun | 2-4pm | Hudak House (Salem)
May 19 Mon | 5-8pm | Corner 14 (Oregon City)
May 20 Tues | 6-8pm | Coria Estates (Salem)
May 22 Thurs | TBA
May 23 Fri | 6-8pm | Kopitos Restaurant (Newberg)
May 24 Sat | 11am-12:30pm | Indy Saturday Market (Independence)
May 24 Sat | 7-9pm | Epilogue Kitchen and Cocktails (Salem)
May 25 Sun | 12-4pm | Cana’s Feast Winery (Carlton)
May 28 Wed | 3-4pm | Private Event (Springfield)
May 29 Thurs | 4-6:30pm | Private Event (Salem)
May 30 Fri | 5-7pm | The Inferno Restaurant (Independence)
May 31 Sat | 2-4:30pm | Pudding River Wine Cellars (Salem)
May 31 Sat | 7-9pm | The Gallon House (Silverton)
June 2025
June 4 Wed | 5-8pm | North Third (Stayton)
June 7 Sat | 1-4pm | Van Duzer Vineyards (Dallas)
June 8 Sun | 3-6pm | High Water Grill* (Silverton)
June 12 Thurs | 5-7pm | Sokol Blosser Vineyards* (Dayton)
June 13 Fri | 7-10pm | Farrar’s Bistro (Vancouver)
June 14 Sat | 1-4pm | Potter’s Vineyard (Newberg)
June 15 Sun | 10am-12pm | Gilgamesh: The River (Independence)
June 19 Thurs | 5-7pm | Benedetto Vineyards (Dallas)
June 20 Fri | 2-3pm | Private Event (Newberg)
June 20 Fri | 7-10pm | The Gallon House (Silverton)
June 21 Sat | All Day | Make Music Day* (Salem)
June 27 Fri | 4-7pm | J. Christopher Wines (Newberg)
June 28 Sat | 1-4pm | Cubanisimo Vineyards (Salem)
June 28 Sat | 4-9pm | Private Event (VandenDries Wedding)
July 2025
July 3 Thurs | 5-7pm | Park & Main (Carlton)
July 4 Fri | 1-2pm | July 4th Festival (Monmouth)
July 5 Sat | TBA | Kopitos Restaurant (Newberg)
July 18 Fri | 2-3pm | Private Event (Keizer)
July 11 Fri | 7-10pm | Farrar’s Bistro (Vancouver)
July 12 Sat | TBA | Corner 14* (Oregon City)
July 17 Thurs | 5-7pm | Benedetto Vineyards (Dallas)
July 18 Fri | 5-10pm | Private Event* (Tony and Sarah)
July 19 Sat | 7-10pm | Farrar’s Bistro (Vancouver)
July 20 Sun | 10am-12pm | Gilgamesh: The River (Independence)
July 20 Sun | 2:30-TBA | TBA (Salem)
July 25 Fri | 7-9pm | Hops on Tap (Tigard)
July 26 Sat | 1-4pm | Cubanisimo Vineyards (Salem)
August 2025
Aug 8 Fri | 5-7pm | The Inferno Restaurant (Independence)
Aug 9 Sat | 3-6pm | High Water Grill* (Silverton)
Aug 14 Thurs | 5-7pm | Park & Main (Carlton)
Aug 15 Fri | 4:30-7:30pm | Left Coast Estate (Rickreall)
Aug 16 Sat | TBA | Kopitos Restaurant (Newberg)
Aug 17 Sun | 10am-12pm | Gilgamesh: The River (Independence)
Aug 23 Sat | 7-9pm | The Gallon House (Silverton)
Aug 24 Sun | 6-10pm | Private Event (Maria Party)
Aug 29 Fri | TBA | Historic Grand Theater* (Salem)
Aug 30 Sat | 1-4pm | Cubanisimo Vineyards (Salem)
Aug 31 Sun | 2-4pm | Benedetto Vineyards* (Dallas)
September 2025
Sept 12 Fri | 7-9pm | Hops on Tap (Tigard)
Sept 13 Sat | 5-7pm | West Hills Vineyards (Salem)
Sept 14 Sun | 1-4pm | Cubanisimo Vineyards (Salem)
Sept 18 Thurs | 5-7pm | Park & Main (Carlton)
Sept 19 Fri | 5-7pm | The Inferno Restaurant (Independence)
Sept 20 Sat | TBA | NASO (Portland)
Sept 21 Sun | 10am-12pm | Gilgamesh: The River (Independence)
Sept 26 Fri | 2-3pm | Private Event (Keizer)
Sept 26 Fri | 7-9pm | Front Street Station* (Salem)
Sept 27 Sat | TBA | Stomp By Croft Vineyards* (Salem)
October 2025
NEW ZEALAND/AUSTRALIA TRIP UNTIL 2027
Additional Venue Info**:
– Apr 9 Wed | 5-7pm | NASO (Portland) 21+ Only
– Dates and Times may be subject to change — check back for updated info!
– Most Vineyards/Wineries are all ages with a 21+ adult, reservations highly recommended (and most are dog-friendly outside!)
**Be sure to always check directly with the venue for age/animal restrictions
About Me:
If you’re a fan of Jack Johnson and Jason Mraz… Dylan Santiago brings down-to-earth SoCal vibes with his tenor voice & baritone ukulele. Inspired by his world travels, he writes illustrative lyrics to memorable melodies to be happily enjoyed by a wide audience. A true local/independent artist, Dylan represents the Pacific Northwest by playing over 100 shows a year for appreciative audiences in a variety of venues.
Don’t miss out — come and enjoy the party!
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Contact:
Dylan@DylanSantiagoMusic.com
503-428-3559