September and October

Celebrate autumn with family-friendly fun, shopping, and seasonal surprises in Historic Downtown Chelan. Fall Into Downtown is a seasonal celebration in Historic Downtown Chelan. Local shops, restaurants, and community spaces are joining together to welcome fall with activities, treats, and plenty of small-town charm.

Festivities

September 1st-30th
Discover downtown in a whole new way! Sign up for our digital scavenger hunt and visit every participating location to take a picture and get entered in a gift basket giveaway!
Sign up
Oct 2nd-4th
Step outside and shop the best of downtown! During Chelan’s annual Fall Sidewalk Sale, local shops bring their bargains, specials, and seasonal finds out onto the sidewalks for a fun, open-air shopping experience. Stroll through Historic Downtown Chelan, discover hidden gems, and enjoy unbeatable deals from your favorite merchants.
Arts Market on Emerson
October 10th from 10 AM – 4 PM
Celebrate creativity in the heart of downtown! The Chelan Arts Market brings together local artists, makers, and crafters for a vibrant open-air showcase. Browse unique works of art, handmade goods, and one-of-a-kind gifts while enjoying the charm of Historic Downtown Chelan.
October 24th from 3PM – 7 PM
Historic Downtown Chelan gets a grown-up twist this Halloween season!
Adult Trick-or-Treat (Free): Stroll through downtown in costume and collect treats, specials, and spooky surprises from participating businesses. It’s a playful, no-cost way to celebrate the season with friends.
Corks and Costumes (Ticketed): Sip and savor your way through boutique shops and tasting rooms while enjoying pours from local wineries. A perfect pairing of Chelan’s downtown charm and world-class wine.
Buy tickets here
Family Trick or Treat in Historic Downtown Chelan
October 31st from 5-7 PM
Bring the kids downtown for a safe, fun, and festive Halloween tradition! During Chelan’s Family Trick-or-Treat, local businesses open their doors to little ghouls and goblins, handing out candy and goodies along the way. Streets come alive with costumes, laughter, and plenty of small-town charm.
Nate Weakley - Oct 3rd (12PM-2PM)
Lance Tigner - Oct 3rd (1PM-3PM)
Laura Belanger - Oct 3rd (2PM-4PM)
Eric Link - Oct 10th (12PM-2PM)
Dan Quigley - Oct 10th (1PM-3PM)
BassICally - Oct 10th (2PM-4PM)
Dan Quigley - Oct 17th (12PM-2PM)
Brittany Jean - Oct 17th (1PM-3PM)
BassICally - Oct 17th (2PM-4PM)
Dan Quigley - Oct 24th (1PM-3PM)
BassICally - Oct 24th (4PM-7PM)

September Stroll

Come downtown this month and try your luck in the FREE September Stroll Scavenger Hunt! Take a picture of your favorite thing or moment at each participating location for a chance to win a prize! Sign up below and begin today!

Proxi Maps

OCTOBER 24, 2026

Wine Walk (ticketed) | 3PM-7PM

Spend the afternoon in Historic Downtown Chelan, moving from stop to stop—each one offering a new pour and a new experience.
A festive, grown-up take on trick-or-treat.

Ticket Price: $40

Includes: 8 tastings, commemorative logo wine glass and canvas tote.

Learn more

Adult Trick-or-Treat (FREE) | 3PM-7PM

Throw on your best costume and hit the streets for treats, specials, and spooky surprises from participating businesses. Plus, strike a pose and enter our Social Media Photo Contest for a chance to win downtown prizes!

Hosted by:

Wine Walk Locations

Woody’s Classic Man
110 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Starry Owl
133B E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Lake Life
146 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Elevate Home
208 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

The Shirt Shop
140 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Willow
119 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Whaley’s
206 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Culinary Apple
109 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Walkin’ on Woodin
210 Woodin Ave, Chelan, WA, 98816
Pouring: TBD

Lake Chelan Sports
132 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Retro Pony
119A E Woodin Ave, Chelan, WA 98816
Pouring: TBD

Lush Life
N Emerson St, Chelan, WA 98816
Pouring: TBD

Check In & Bottle Shop

Lake Chelan Chamber of Commerce
216 E Woodin Ave, Chelan, WA 98816
Pouring: TBD

⁓ Live Music ⁓

Nate Weakley

October 3rd

12PM-2PM

Nate honed his craft in New Orleans, Nashville and the PNW, blending country, folk and rock.

Learn more

Lance Tigner

October 3rd

1PM-3PM

I am a 45 year veteran of the musical performance industry. My experience as a performer is extensive, encompassing solo performances, ensembles of all sizes and productions.
My musical library is varied and eclectic. I enjoy being a musician and a performer.

Learn more

Laura Belanger

October 3rd

2PM-4PM

Drummer of In Danger Lead Vox in Sound City Silence Sometimes I exist outside of work.

Learn more

Eric Link

October 10th

12PM-2PM

I play a variety of old, new, and original songs on guitar, mandolin and Dobro. Van Morrison, Sublime, Lil Nas X, Chris Stapleton, Eagles, Third Eye Blind, John Denver, Garth Brooks, The Beatles, The Wallflowers, Ed Sheeran, Prince, AC/DC, Neil Young,etc

Learn more

Dan Quigley

October 10th

1PM-3PM

Hello friends, I often play around the Chelan-Wenatchee-Leavenworth area at various wineries

Learn more

BassICally

October 10th

2PM-4PM

Hey there, I'm BassICally (Ally Paige), and I’m a Singer & aspiring EDM Music producer in WA and beyond!

Learn more

Dan Quigley

October 17th

12PM-2PM

Hello friends, I often play around the Chelan-Wenatchee-Leavenworth area at various wineries

Learn more

Brittany Jean

October 17th

1PM-3PM

Hello! I’m Brittany, a singer, songwriter, and storyteller. I call the beautiful Pacific Northwest home, currently living in a little, apple town on the Columbia River in Washington. Having grown up in Home Sweet Illinois and a very different landscape, the wild beauty of my new home base will never get old.

Learn more