Let me plan your weekend: Fall itinerary ideas
If you know me, you know I love planning itineraries—for my friends, my family, and really anyone who will let me. So now I’m having some fun and doing it for you, too.
Here are six upcoming fall weekends I’d plan if they were mine: vintage markets, cliffside sunsets, creative workshops, festive nights out, and all the magic of Central Washington woven in.
Which weekend are you interested in?
October 15-18
🛍️🌿Vintage Finds, Autumn Gardens & Harvest Dinner
If your perfect fall weekend includes vintage treasure hunting, wandering autumn gardens while listening to live music, a gorgeous wine‑paired harvest dinner, and a little retro arcade fun at night, this one is for you. It’s equal parts relaxing and adventurous — a little shopping, a little sipping, and a whole lot of Central Washington charm.
Thursday, Oct. 15 — Music in the Gardens + Dinner in Town
Music in the Gardens: Cut out of work a little early and ease into the weekend at Music in the Gardens at Brick House Nursery (5:30–7:30pm) in Ellensburg, WA. The gardens are lush, peaceful, and absolutely stunning in October. Sip a glass of Sagecliffe wine while listening to Jodi Ryan’s live set. They also have an incredibly cute gift shop to kickstart your shopping weekend.
Dinner at the Huntsman Tavern: Afterward, head into downtown Ellensburg for dinner at The Huntsman Tavern. The design and ambiance is upscale-but-cozy and the cuisine is American with a southwest flare, plus a whiskey library of 700+ bottles.
Friday, Oct. 16 —
Unwind at the Wild Horse
The Wild Horse: Spend the day fully relaxing at the Wild Horse vacation home. Breakfast on the back patio, an afternoon soak in the hot tub, an evening grilling dinner on the Blackstone grill, and a glass of wine by the fire. There is absolutely nowhere you need to be.
Saturday, Oct. 17 — Junk-tiquen + Harvest Dinner
Junk-tiquen in the Burg: Spend the day at Junk-tiquen (9am–4pm), the once‑a‑year vintage market at the Kittitas Valley Event Center. Spend the day browsing a whole mix of antiques, vintage finds, handmade goods, home décor, sweet treats and more from 60+ vendors—and wonder how you’re going to fit everything you bought into the car. Purchase tickets at the door for $15 per person. Children 12 & under are free.
Sagecliffe Harvest Dinner: That evening, head to Sagecliffe Resort for their Harvest 4‑Course Wine Paired Dinner (6:30pm). Set against the spectacular backdrop of the Columbia River Gorge, each course is paired with a Sagecliffe wine and accompanied by live violin music. It’s warm, intimate, and the perfect fall evening. Reserve Your Place for $125 per person
The Wild Horse: End the night back at the house playing in the epic retro arcade game lounge.
October 23-25
🔥🍷 Burn & pour Weekend
Friday, Oct. 23 — Settle in + sunset
If crafting something beautiful, sipping wine, and leaning fully into fall sounds like your perfect weekend, Burn & Pour is for you. A hands‑on creative workshop, a little fire, a little wine, and sweeping Gorge views.
Villa Vantage: Arrive at the Villa Vantage vacation home and settle into the rhythm of the weekend. A sunset soak, a simple dinner, and a lovely night in the living room looking out over the river with music and conversation.
Saturday, Oct. 24 — Hat Burning Workshop + Wine Tasting
Branding workshop: Start your morning with mimosas and a private custom branding workshop, right at the dining table, led by Lindsey of Blonde Dog 509. She brings everything directly to the home—hats, handbags, tools, embellishments—so all you have to do is sip, create, and enjoy. Choose your canvas and make something meaningful, unique, and totally you.
Cave B Winery: Later in the afternoon, build a charcuterie board (or buy one there), throw on your newly customized hat or handbag, and head to Cave B Winery (11am–6:30pm on Saturdays) for wine tasting and stunning vineyard and Columbia River Gorge views.
Villa Vantage: End the evening back at Villa Vantage around the fire table on the cliffside deck, overlooking the Columbia River.
October 30 - November 1
🥃🎃 Spirited Halloween Weekend
If you love a little fall magic, whether that’s trick‑or‑treating with the kids or sipping whiskey in a moody bar, this weekend at The Desperado is built for you.
Friday, Oct. 30 — Sauna + Stargazing
The Desperado: Check into the Desperado vacation home and ease into Halloween weekend with a sauna session and stargazing from the hot tub. The Desperado’s moody aesthetic makes it the perfect place to kick off a spirited fall escape.
Saturday, Oct. 31 — Trick-or-Treat Harvest Fest or Whiskey Tour + Dinner
Option 1 — Family-Friendly Halloween
Downtown Trick-or-Treat Harvest Fest: Start the afternoon in downtown Ellensburg for the annual Trick-or-Treat Harvest Fest. Grab your candy bag and map at Unity Park, then wander through the historic district collecting treats from local businesses. Kids will love Touch‑A‑Truck on Pearl Street and the live performances by The Dancing Witches and Ellensburg Dance Ensemble.
Option 2 — Adults-Only Whiskey Weekend
Woodinville Whiskey Co. Quincy Tour: If you’re traveling without kids, head to Woodinville Whiskey Co.’s Quincy production facility for the 4pm tour. Get a behind‑the‑scenes look at where their whiskey is aged and bottled, followed by a tasting, and even an option to fill your bottle directly from the spigot drilled into the barrel for a true, straight-from-the-barrel experience.
Sagecliffe Halloween Dinner: After the tour, head to Sagecliffe Resort (6pm) for a specially curated multi‑course Halloween dinner, with each course paired with selections from Woodinville Whiskey. Costumes encouraged, but entirely optional.
Halloween Night: Return back for a fun night at the Desperado. The whiskey bar is basically made for this: dark, cozy, and perfect for a Halloween playlist, a cocktail, and a little karaoke. Kids can grab the microphones, adults can grab a drink, and everyone can throw on a costume and make a night of it.
November 13-15
🎄🛍️ Christmas Comes Early Weekend
If you’re the kind of person who gets a little spark of joy the moment the Christmas décor hits the shelves, this weekend is your official permission slip to start celebrating early.
Friday, Nov. 13 — Festive Dinner + Arcade Night
Wild Horse: Check into the Wild Horse vacation home and kick off the weekend with a festive meal in the fully stocked kitchen — think homemade pizza, a holiday cocktail, or even a batch of cookies to keep the spirit going all weekend long.
End the night with some friendly competition in the arcade game room while blasting holiday music.
Saturday, Nov. 14 — Holiday Market + Christmas Wonderland
Vantage Coffee Co.: Grab your favorite coffee (or one of their delicious autumn drink specials) at nearby Vantage Coffee Co. for your drive into Ellensburg. Let the holiday shopping anticipation set in.
Ellensburg Holiday Market: Start your day at the Ellensburg Holiday Market, held only one day a year, from 9am–3pm. Browse local vendors, hunt for handmade, vintage, boutique, unique gifts, and find a few things you definitely weren’t planning to buy. It’s festive, charming, and the perfect way to ease into the season.
Dusty’s Nursery Holiday Open House: Then head to Dusty’s Nursery (9am–5pm), where the barn transforms into a full‑on Christmas wonderland. Wander through the decorations, sip cider, snack on cookies, browse the storewide sale, and pick up a few gifts. There’s free gift wrapping, door prizes, and enough Christmas magic to make you forget Thanksgiving hasn’t even happened yet.
The Wild Horse: Return to the Wild Horse for an evening soak in the hot tub, followed by a cozy movie night with a few holiday classics.
Open a bottle of wine and feel good about the fact that you got beautiful holiday gifts for everyone all while supporting local.
December 3-6
🎄✨ Handmade Holiday Weekend
If your perfect December weekend mixes creativity, hands‑on fun, playful outdoor activities, and plenty of cozy downtime, this one is for you. At Villa Vantage, no one will miss being on a screen—there’s too much beauty to make, explore, and enjoy.
Thursday, Dec. 3 — Settle In + get cozy
Villa Vantage: Arrive at the Villa Vantage vacation home and ease into the weekend with a homemade dinner in the large kitchen, a sunset soak in the cliffside hot tub, and a lovely night of conversation around the fire pit overlooking the river. Put on a holiday playlist, pour a glass of wine, and let the weekend begin.
Friday, Dec. 4 — Handmade Jewelry + Cliffside Fun
Stampede Jewelry Workshop: Make a few appetizers, pour a drink, put on some good music, and spend a few hours learning to silversmith right at your vacation home. This private jewelry‑making workshop is led by an instructor from Stampede Jewelry — beginner‑friendly, hands‑on, and incredibly fun.
Choose between a stacker ring or a stone ring/pendant, and leave with a one‑of‑a‑kind piece you made yourself. It’s creative, memorable, and the perfect way to kick off the holiday season.
Villa Vantage: Keep the fun going all afternoon without ever leaving the property. Villa Vantage offers a cliffside driving range, a putting green, and a full croquet course — the perfect mix of playful competition and stunning views.
Saturday, Dec. 5 — Breakfast + Wreath Workshop + rest
Kittitas Café: Start your morning at Kittitas Café — an unexpectedly cool spot with an eclectic vibe and friendly service, tucked into the heart of the tiny rural town of Kittitas, WA. Grab a specialty coffee, one of their fresh pastries (they have different flavors every day!), or a full-on breakfast—their menu puts an adventurous twist on the classics, and I always suggest ordering something off the seasonal menu (it never disappoints).
Woodland Findings: Join Dawn Ambrose of Woodland Findings for a holiday wreath‑making workshop in an indoor space tucked into the woods on the outskirts of Ellensburg, WA. Gather greenery, fasten it to a wire frame, and decorate your wreath with natural elements.
It’s hands‑on, grounding, and a beautiful way to reconnect with nature during the busiest season of the year.
The Ranch: Stop by The Ranch in Vantage, WA on the way back and pick up some premium fresh cuts of steak. All the beef comes from their local ranch and they can grill the steaks for you, or take it home to grill on the patio. Alternatively, you can just order a smash burger (it’s the best in Washington state) and their delicious tallow fries and call it a day. Done and done.
Villa Vantage: Head back to Villa Vantage for an evening of pure relaxation with infrared sauna, cold plunge, hot tub, and multiple cliffside hangout spaces with glowing fire pits.
December 10-13
💋 🧖♀️ Girls’ Holiday Night Out + Spa Weekend
If all you really need is your girls, a little holiday sparkle, and a weekend away to reset before the chaos of December, this one’s for you.
Thursday, Dec. 10 — Girls’ Night Out + Dinner in Town
Holiday Girls Night Out: Leave work early and head to downtown Ellensburg for Holiday Girls Night Out (3pm–9pm). Downtown businesses will stay open late, offering exclusive discounts, special promotions, giveaways, refreshments, live entertainment, pampering experiences, and festive surprises throughout the evening. It's the perfect opportunity to shop local and cross a few names off your holiday shopping list while enjoying a fun night out.
Dinner + Cocktails: While in downtown Ellensburg, walk over to Julep Southern Kitchen & Cocktail Bar (21+) for dinner and the best festive drinks in town. The cuisine is Southern comfort food and the creative craft cocktails they serve up rotate seasonally. Voted best cocktails in Kittitas County multiple years running!
The Desperado: After dinner, check into The Desperado vacation home and settle in for a weekend of relaxation, connection, and a little indulgence.
Friday, Dec. 11 — Brunch + Spa Day + Sauna
Tendrils Restaurant: Start the morning with brunch at Tendrils Restaurant at Sagecliffe in Quincy, WA— a cozy, upscale dining experience with stunning views of the Columbia River.
Sagecliffe Spa: Spend the afternoon at the Sagecliffe Spa with massages, body wraps, champagne, and light bites. This is uninterrupted girl time at its finest — catching up, unwinding, and letting the holiday stress melt away.
The Desperado: Continue the relaxation back at The Desperado with a rooftop sauna session and a little aromatherapy with essential oils—all with beautiful Columbia River views.
Saturday, Dec. 12 — Relaxed Morning + Scenic Walk + Hot Tub
Sleep In: No plans, no alarms, just zzzzzzzzzzz. Stay in your pajamas, m
ake coffee, and enjoy a morning conversation with your girls on the cozy couch.
Palouse to Cascades Trail: Drive to the nearby trailhead and take an easy walk on the Palouse to Cascades Trail (it’s almost totally flat in this area)— including the pedestrian bridge that crosses over the Columbia River. It’s peaceful, scenic, and the perfect amount of crisp fresh air.
The Desperado: Return to The Desperado for a long soak in the hot tub before settling in for a cozy night. A nice dinner at the house, a favorite holiday rom-com, some board games, or…if you get a burst of energy, sing your heart out to all the best Mariah Carey holiday tracks on the karaoke stage.