A softly lit holiday evergreen beside warm neighborhood windows and a rain-darkened courtyard in Issaquah.

Issaquah's Holiday Season Starts Up the Hill, Then Works Its Way Down to Front Street

Issaquah's holiday season begins up in the Highlands this evening. Over the next three weeks it moves down to the valley floor, settling into Front Street over Thanksgiving weekend and then into the Depot, Gilman Village and Pickering Barn in early December. If you follow that order, you get a clear sense of which part of town is busy on which weekend.

The first evening is tonight, Thursday, November 19.

Tonight, the season starts on Village Green

The Issaquah Highlands Holiday Tree Lighting runs from 5:00 to 6:30 p.m. at Village Green Park, 2550 NE Park Drive. The big tree is scheduled to light at 5:15 p.m. That's early, so the main moment happens soon after most people get home from work.

The event fits a lot into ninety minutes. There's free hot chocolate, apple cider and cookies, carolers, and photos with Santa and Mrs. Claus. The Issaquah Police Department and Eastside Fire & Rescue will also be there. Highlands Fiber Network, Puget Sound Energy and Issaquah Ice Cream Trike are the sponsors.

The timing also leaves room for a second stop. Village Theatre's Issaquah run of Come From Away began November 10 and continues through December 27, and tonight's show starts at 7:30 p.m. The tree lighting ends at 6:30, so you can see the tree lit in the Highlands and still drive down to the theater before curtain.

The Highlands has one more event before the season moves downhill. The Village Green: Holiday Pop-Up runs Sunday, November 22, from 10:00 a.m. to noon at Blakely Hall, the same 2550 NE Park Drive address, with local artisans and vendors. It's a two-hour Sunday morning event, and it's the Highlands' last scheduled holiday gathering of the season.

Thanksgiving weekend, Front Street takes over

The day after Thanksgiving is when downtown starts. The rest of the season runs on the valley floor.

The center of it is the Historic Shell Holiday Shop at 232 Front Street North, which opens Friday, November 27. It's open noon to 6 p.m. Fridays through Sundays from Thanksgiving to New Year's Eve. More than 30 local artists sell jewelry, ceramics, cards, ornaments, journals, stickers and pins. Alison Lang of So, There curates the shop with the Downtown Issaquah Association, and this is its 11th year. No other downtown holiday event runs as long. It stays open every weekend after the Highlands tree is lit and after the December events wrap up.

That same weekend, the Historically Hip Artisan Market holds Shop Local Saturday on November 28 and Artist Sunday on November 29. Both run 11:00 a.m. to 4:00 p.m., and the city lists both at the Historic Shell Station, 228 Front St. N.

On the same Friday, the Issaquah Reindeer Festival returns to Cougar Mountain Zoo for its run from November 27 through December 23. It's open daily from 10:30 a.m. to 4:30 p.m. or dusk, depending on the weather. Santa is there for the whole run, and photos with him require an additional minimum donation.

Here's how that weekend falls by day:

Day Front Street Cougar Mountain Zoo
Friday, Nov. 27 Shell Holiday Shop opens, noon–6 p.m. Reindeer Festival opens, 10:30 a.m.–4:30 p.m. or dusk
Saturday, Nov. 28 Shop Local Saturday, 11 a.m.–4 p.m.; Shell Holiday Shop, noon–6 p.m. Reindeer Festival
Sunday, Nov. 29 Artist Sunday, 11 a.m.–4 p.m.; Shell Holiday Shop, noon–6 p.m. Reindeer Festival

On Saturday and Sunday the Front Street hours overlap from noon to 4, so both artisan events are open at the same time. The zoo closes at 4:30 p.m. or dusk, which means a morning with the reindeer still leaves the afternoon for Front Street.

In December, the season settles in downtown and along Gilman

After Thanksgiving, three dated evenings and mornings carry the season through the valley. Each one is in a different part of downtown.

  1. Thursday, December 3, 6:00–7:30 p.m.: Caroling at the Depot. The Downtown Issaquah Association hosts its holiday sing-along at the Issaquah Depot Museum, 78 1st Ave NE. Santa and Mrs. Claus will be there for photos. Hot chocolate and candy canes are provided, and you're invited to bring a ukulele or a tambourine.
  2. Saturday, December 5, 6:00–9:00 p.m.: Gilman Village Wine Walk. The Gilman Village Merchants Association is pairing tastings from local wineries with live music and holiday shopping at Gilman Village, 317 N.W. Gilman Blvd.
  3. Saturday, December 12, 9:00 a.m.–2:00 p.m.: Holiday Gift Market. The Issaquah Farmers Market comes back for one winter day at Pickering Barn, 1730 10th Ave. NW, with treats, crafts and art. Eligible food purchases can be made with EBT benefits.

Each of these is set for a different kind of outing. The Depot caroling is on a weeknight and wraps up by 7:30. The Wine Walk is a Saturday night event. The Gift Market is a Saturday morning one. The first two are evening events and the third is in the daytime, so a household could reasonably go to all three.

The longer runs keep going around them. The Shell Holiday Shop stays open Fridays through Sundays, the reindeer are at the zoo until December 23, and Come From Away runs until December 27. The zoo also stays open after Christmas. From December 26 to 30, Santa is gone but the festival continues daily from 10:30 a.m. to 3:30 p.m.

What's changed along Gilman Boulevard this year

The Wine Walk and the Gift Market both draw people to the Gilman Boulevard side of downtown, where several businesses have recently changed. The City of Issaquah's September 30 business update lists what's new.

  • Gilman Glasses is listed as now open. The city's business podcast mentions its unique eyewear.
  • Bellevue Rare Coins opened a new showroom at 1145 NW Gilman Blvd., Suite G-1. It was announced in July and listed as open by the end of September.
  • Dave's Hot Chicken has an Issaquah location page at 730 NW Gilman Blvd.
  • The same update lists Rivian and Evergreen Ford under "Opening Soon or Moving." The podcast describes a planned Rivian showroom and service center and an upcoming move for Evergreen Ford.
  • The update also includes Petco under businesses closing.

One more change is still to come in Olde Town. In September, the Issaquah Spotlight reported that a coffee-and-ice-cream shop is planned for the former Blazing Bagels storefront on Sunset Way and would open next year. The city's September update also lists Issaquah Alps Coffeehouse/Ben & Jerry's under "Opening Soon or Moving."

Mapping the weekends

Taken together, the calendar follows a clear route. The Highlands has November 19 and 22. Front Street and the zoo open November 27. The Depot follows on December 3, Gilman Village on December 5, and Pickering Barn on December 12. If you live up the hill, your biggest night is the first one. If you live closer to the valley floor, most of the season happens within walking or short driving distance in December.

The Shell Holiday Shop is the only event open across most of that stretch. It stays open Fridays through Sundays, noon to 6 p.m., until New Year's Eve, so it's still there on weekends after the dated December events are over.

From the tree lighting tonight to the last Front Street Sunday of the year, we're glad to call Issaquah part of our community, and we hope this calendar helps you plan your season. If a move is on your mind for the new year, Diana Patterson and the team are happy to talk it through calmly and without any pressure. Just reach out through Contact Us whenever you're ready.

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