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! Pick up a September Stroll Passport at any participating business, then wander through our charming shops, cafés, and boutiques to collect stamps along the way. Complete your passport and you’ll be entered to win a locally curated gift basket filled with goodies from our merchants

  • Oct 4th & 5th

    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 18th 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 25th from 4 PM – 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.

    Downtown Wine Walk (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.

  • 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.

  • Erin McNamee - Oct 4th (4:30-7:00pm)

    Greg King - Oct 11th (10am-1pm)

    Brittany Jean - Oct 11th (12-3pm)

    Erin McNamee -Oct 11th (12-3pm)

    Kevin Jones - Oct 18th (10am-12pm)

    Brittany Jean -Oct 18th (10am-12pm)

    Owen Barnhart - Oct 25th (5pm-7pm)

    Coventry - Oct 25th (5pm-7pm)

OCTOBER 25, 2025

Sip, stroll, and savor the flavors of the season! Our Fall Wine Walk brings together the best local wineries for an afternoon of tasting as you explore charming shops and cozy tasting rooms in the charming historic downtown Chelan. Enjoy crisp whites, bold reds, seasonal blends, live music, and the magic of harvest season. Whether you’re a wine enthusiast or simply looking for a perfect fall outing, the Fall Wine Walk is a toast to community, connection, and the beauty of autumn. 🍷 

Presented by:

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Wine Walk Locations

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Whaleys General Store

Fall Into Downtown Is Brought To You By:

French Quail Too

Lake Chelan Sports

Layla’s Bar + Kitchen

Lush Life

Rocky Pond Winery Tasting Room

Shirt Shop Plus

Culinary Apple

Support our efforts to maintain an active downtown with rich history, a vibrant community and endless outdoor adventure.

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