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In Historically Hip Downtown Issaquah, don’t let the holiday rush steal time from the experiences that truly matter. Savor the season by shopping small with friends in artistic boutiques filled with one-of-a-kind gifts, dining at family-owned spots ranging from cozy diners to elegant restaurants, and wrapping up your day by settling into the regal atmosphere of a world-class theatre performance.
To further the fun, join us for a jolly night of holiday cheer of Caroling at the Depot at the Issaquah Depot Museum for Issaquah’s favorite holiday tradition — a merry evening filled with music, laughter, and festive fun on Dec. 4 from 6 to 7:30 p.m.
Snap photos with Santa & Mrs. Claus and capture the holiday magic. Warm up those vocal cords. We’ll be leading a joyful sing-along of all your favorite holiday classics. Bring your ukulele, tambourine, or just your singing voice, and join the chorus of holiday spirit. Santa hats and festive outfits are encouraged. Hot chocolate and candy canes for everyone who joins the fun!
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Santa and Mrs. Claus Issaquah Schedule:
--November 29, 10am - noon Historic Shell Station 232 Front Street N.
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--November 30, 11 am - 2 pm Historic Shell, 232 Front Street N.
--December 4, 5:30 pm - 7:30 pm at Caroling at the Depot
--December 6, 11:30 am - 2:30 pm at Grange Supply
--December 13 and December 20, 11 am - 2 pm Gilman Village
--December 14, 11 am - 1 pm Historic Shell
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Experience
Front Street Smarts
Downtown Issaquah has some of the most entertaining and educational spots on the Eastside. Head on over to experience so much fun that you won’t learning. Whether immersing in tea, chocolate, or wine, you'll walk away sated and savvy.
At Experience Tea, discover a world of flavor and endless variety—there’s something for every tea lover here! Explore premium teas, hands-on classes, and quality tea tools designed to enhance your tea journey.
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Dining
Issaquah Eats
In Downtown Issaquah, food is the ultimate equalizer. People come together from all walks of life. The greatest memories are when gathered around the table.
Rev up your taste buds by visiting the Issaquah Restaurant Spotlight series on YouTube. Watch local celebrity and business owner Troy Kline eat and tell about a variety of local fare, shown here at Fins Bistro.
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Experience
Oenophiles gather at Capri Cellars not just for the uncorking, but for the learning! Sign up for classes for the beginner, enthusiast, and professional.
While you're there, you'll have to varietals from all over the world. It's a wine bar, a bistro and a store all in one. You get to experience the vints and vibe, and imbibe at the same time.
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Experience & Eat!
Learning has never been so fun! Take classes, or a guided tour through Boehm's chocolate factory and experience the art of handmade chocolate making—complete with delicious samples along the way. You’ll also visit the charming alpine chalet where its founder once lived and explore the picturesque High Alpine Chapel that completes this sweet and scenic experience
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Shop Local & Win Big through the Issaquah Chamber of Commerce
From November 24 – December 14, 2025, every time you support Issaquah’s shops, restaurants, and local services, you could win cash prizes up to $1,000!
Each $25+ purchase earns you another entry—so the more you shop, the more chances you have to win. Just save your dated receipt (printed or emailed) from each qualifying purchase—it’s your ticket to enter!
Shop early, shop often, and let your holiday spirit pay off in more ways than one!
| | Local writers share their stories and books with browsers Sunday, Nov. 30, 2024, at La– Z–Boy Home Furnishings & Decor store, 628 Front Street N, Issaquah, from 12-3 p.m. | |
You never know where the perfect gift might be hiding! Downtown’s boutiques come in all shapes and sizes—each with its own surprises waiting to be discovered.
Pop into Pelage Medi-Spa for unique treasures crafted by artisans, quirky whatnots, and beauty products dreamed up by scientists. Wander through local restaurants and you’ll spot original art by talented local artists adorning the walls. A little exploring makes the hunt for the perfect gift all the more fun!
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More Gifting!
No better time than the holidays to show your love through gifts! The Historic Shell Holiday Shop is open Friday through Sunday, Thanksgiving until the end of December. From noon to 6 p.m.
And don't forget the Historically Hip Artisan Markets Saturday & Sunday after Thanksgiving and December 13-14.
| | | The Gilman Village Shopping District, a landmark for almost half a century and a significant part of the city's Creative District, features shops, restaurants, personal services, and even a preschool. All are housed in buildings and structures preserved from Issaquah’s historic past. | | | Chick’s Shoes and Service opened on Mercer Island in 1949, founded by Chick Tabit—a third-generation cobbler who learned his craft alongside his father and grandfather. Today, the fourth and fifth generations of the Tabit family carry on that legacy, expanding the business to include pedorthic and orthopedic services in addition to a retail shop filled with comfortable, supportive footwear. If your feet need relief, this is the place to go. | | | |
Big Picture features a plush comfortable lounge, a luxurious 33-seat theatre, serious smashburgers, potent martinis and movie-themed cocktails to enjoy during blockbuster shows. Don't forget the crispy tots. They're legendary.
With its thoughtful details and luxurious touches, Big Picture redefines the movie-going experience. Guests can have martinis delivered directly to their theater seats at the precise moment they request them. Popcorn arrives in a champagne bucket lined with white napkins and topped with melted truffle butter, while candy is served in a chilled martini glass. There are no commercials before the film, and every piece of furniture and the bar itself were custom-designed to evoke the feel of a high-end hotel.
Coming Nov. 20: Wicked for Good.
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Get ready for a hilarious workplace revenge comedy from the one and only Dolly Parton at Village Theatre!
When three fed-up coworkers decide they’ve had enough of their sexist, egotistical, lying boss, they hatch a wild plan to get even—and chaos and laughter quickly follow.
Set in the fun-loving “Rolodex era” of shag rugs, disco, and pet rocks, 9 to 5: The Musical is based on the hit 1980 film and features Dolly’s iconic title song plus 18 brand-new tunes she wrote herself. Big-hearted, outrageous, and full of energy, this show celebrates teamwork, self-respect, and standing up for yourself—all with a wink, a laugh, and a whole lot of toe-tapping fun.
Running Nov. 18-Jan. 4 in Issaquah.
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Why Your Support Matters
| | | When you give to the Downtown Issaquah Association (DIA), you’re investing directly in the heart of our community. DIA’s work strengthens local businesses, creates welcoming public spaces, and brings people together through events that make downtown vibrant and connected. We are a 501c3 nonprofit organization, which may be eligible for employer matching funds. | | See you soon in Historic Downtown Issaquah! | | The Downtown Issaquah Association |425.391.1112 | Execdirector@downtownissaquah.com | | | | |
