The 2025 Grown-Up’s Guide to the Holidays: Portland & Beyond

by Cassidy Campanian

✨ The 2025 Grown-Up's Guide to the Holidays: Portland and Beyond

Festive lights with holiday candles on a wood table

If you're looking to trade hot cocoa lines for something a bit more grown up, December around Portland offers no shortage of options. Think festive cocktails, wine country escapes, winter markets, and a few great excuses to dress up before New Year's Eve. Here are the events that set the tone for the season.

✨ Shows, Wine Events & Pub Crawls

‘Twas The Night Before Nutcracker – Burlesque Show

When: November 20, 2025 – January 11, 2026
Where: Can-Can Paris Theater, SW Portland
What: A cheeky, adults only twist on The Nutcracker with burlesque, comedy, and cocktails in a historic downtown theater.

Sippin' Santa Holiday Pop-Up

When: November 17 – December 31, 2025
Where: The Social Spoon, SW Portland
What: A tropical themed holiday bar with over-the-top glassware, festive rum drinks, and cozy date night vibes.

Portland Miracle Pop-Up

When: November 19 – December 30, 2025
Where: Deadshot, SE Portland
What: A Christmas cocktail bar takeover with themed drinks, vintage holiday décor, and lots of photo-worthy moments.

Portland Holiday Brewfest

When: December 5–6, 2025
Where: Pioneer Courthouse Square, Downtown Portland
What: A 21+ outdoor beer and cider festival under the city’s big tree with seasonal pours, food vendors, and live music.

St. Johns Ugly Sweater Pub Crawl

When: December 6, 2025
Where: Bars throughout the St. Johns neighborhood
What: A neighborhood crawl with prizes, drink specials, and plenty of ugly sweaters up and down Lombard.

Hip Chicks Holiday Market

When: December 6, 2025
Where: Hip Chicks Do Wine, SE Portland
What: A small, cozy market at an urban winery featuring local makers, wine flights, and seasonal bites.

Winter Market at Tumwater Vineyard

When: December 6, 2025
Where: Tumwater Vineyard, West Linn
What: A wine country holiday market with local vendors, cozy tasting spaces, and views of the surrounding hills.

Deck the Hills – Dundee Hills Holiday Weekend

When: December 6–7, 2025
Where: Various wineries throughout Dundee Hills
What: A weekend of tasting room specials, festive décor, and events at participating Dundee Hills wineries.

Three Feathers Wine Pour at Marco’s Café

When: December 12, 2025
Where: Marco’s Café, Multnomah Village, SW Portland
What: A relaxed evening tasting Three Feathers wines in one of SW Portland’s coziest neighborhood restaurants.

Rudolph the Red Dress Party – Stoller Wine Bar

When: December 12, 2025
Where: Stoller Wine Bar, Newberg
What: A playful dress-code party with red outfits, seasonal pours, and holiday playlists in wine country.

Portland Ugly Sweater Bar Crawl

When: December 13, 2025
Where: Spare Room Restaurant & Lounge, NE Portland
What: A multi-stop bar crawl centered around Spare Room with prizes for the loudest sweaters.

The 2025 Yule Ball

When: December 13–14, 2025
Where: Sheraton Portland Airport Hotel
What: A fantasy themed formal with costumes, dancing, and plenty of Harry Potter-inspired atmosphere.

Oaks Park Adult Skate Nights

When: December 4, 11 & 18, 2025
Where: Oaks Park Roller Rink, SE Portland
What: Throwback roller skating with 21+ sessions, themed music, and plenty of nostalgia.

Sip & Sleigh – Wine & Beverage Walk

When: December 18, 2025
Where: Downtown Portland
What: A self-paced tasting walk featuring participating shops and bars pouring wine, beer, and holiday drinks.

Portland SantaCon

When: December 20, 2025
Where: Downtown Portland & the Pearl District
What: A citywide Santa costume takeover with hundreds of adults in red suits roaming bars and streets together.

The Winery Comedy Tour

When: December 20, 2025
Where: Fullerton Wines Portland Tasting Room, NW Portland
What: A stand-up comedy show hosted inside a tasting room, with wine flights available while you watch.

Paint & Sip at Fullerton Wines

When: December 21, 2025
Where: Fullerton Wines Portland Tasting Room, NW Portland
What: A guided painting class paired with wine, perfect for a low-key date night or girls’ night out.

Pix Pâtisserie – Champagne Class

When: December 28, 2025
Where: Pix Pâtisserie, East Burnside, Portland
What: A deep dive into bubbly with guided tastings and plenty of French desserts to pair.

🎊 New Year's Eve Weekend Events

Pink Martini: New Year's Eve Celebration

When: December 30–31, 2025
Where: Arlene Schnitzer Concert Hall, Downtown Portland
What: A glamorous New Year's concert with Portland’s favorite band and a dressed-up crowd.

Portland City Grill – New Year's Eve Spectacular

When: December 31, 2025
Where: Portland City Grill, Downtown Portland
What: A dressy night out with skyline views, dinner, and New Year's toasts 30 stories up.

Portland’s Premier NYE Bash – Sentinel Hotel

When: December 31, 2025
Where: Sentinel Hotel, Downtown Portland
What: A big hotel party with multiple rooms, DJs, and a very dressed up crowd.

Portland New Year's Eve Bar Crawl

When: December 31, 2025 at 6:00 p.m.
Where: Various participating bars in Downtown Portland
What: A ticketed crawl that hops between several downtown bars so you can sample a little of everything on NYE.

🥂 Have a safe and Happy New Year!

Let's Connect

Cassidy Campanian

+1(971) 645-1071

cassidy@cassidycampanian.com

Image of Cassidy Campanian, Portland Real Estate Agent