A Night on the Town (21+) - Explore Wilsonville
ExploreA Night on the Town (21+)

A Night on the Town (21+)

From Wilsonville wine tasting to the city’s best happy hours, summer is in full swing for the grown ups in your party–day and night. Escape to a vineyard, get a massage, or find your new favorite cocktail with these picks.


  • Oregon wineries
  • Craft breweries
  • Whiskey bar
  • Bowling and arcade games
  • Massage and spa treatments

2 Days

12 Stops

Oswego Grill

Oswego Grill is a happy hour favorite in Wilsonville–and for good reason. The restaurant’s wood-fired grill, seasonal menu rotation and handcrafted cocktails offer a classy take on old favorites.

J Rallison Cellars

The tasting room at J Rallison Cellars offers a friendly, approachable bar for tasting bold red wines cultivated in the heart of Oregon’s wine country.

Boston’s Pub & Grill

Boston’s Pub & Grill is a Wilsonville mainstay with a happy hour worth raving about. Open late, this casual hole in the wall has offered bar fare and beer since 1985. Come hungry and prepare to leave with a to-go box. The portions here are huge!

Twill Cellars 

The modern minimalist interior of Twill Cellars’ tasting room will win you over (the heated patio a close second). With well-appointed misters to keep you cool on a summer afternoon in Oregon, you’ll be hypnotized by the rows of grapes stretching to the edges of the property.

Vanguard Brewing

What’s more Oregon than locally-made craft brews? Featuring a friendly taproom and a community-centric beer garden, we love Vanguard Brewing for a low key outing on a warm summer night.

Three cocktails on the bar counter.
Boston’s Pub and Grill has offered bar fare and beer since 1985. 
Woman picking up a beer at Ordnance Brewing
Ordnance taproom features dozens of brews and an approachable environment. This is where you can meet the locals.

Ordnance Brewing

As soon as you walk into the taproom at Ordnance Brewing, one thing is clear–this is a place to meet the locals. Located just a few miles from the original homestead of the brewery’s founders, this taproom features dozens of brews and an approachable environment.

Ram Restaurant & Brewery

This family-owned (and family-friendly) establishment is known for its burgers and beer. Ram Restaurant & Brewery offers seasonal brews, fried pickles and peanut butter pie while chilling on the patio.

Siren Song Whiskey Bar (Canby)

Visit Siren Song if you’re looking for an option on the swanky side. Here, you’ll find craft cocktails, fine liquors and an elevated aesthetic. If you’re looking for a good time and a great atmosphere, look no further.

Bullwinkle’s After Dark

Hosted only a handful of times every year, Bullwinkle’s After Dark is an occasion worth clearing your calendar for. Open to guests 21 and older, kids at heart will have the run of the facility with pizza, bowling, mini golf, arcade games and more.

McMenamins Old Church & Pub

A visit to any McMenamins location is an experience to remember, and the Old Church & Pub in Wilsonville is no different. Open late with multiple daily happy hours, enjoy a visit for bar fare and the eclectic decor that McMenamins is known for. Summer nights are even sweeter from the patio.

Divine Complexions Spa

In Wilsonville, rest is not a reward to be earned. Our preferred method of self care is a treatment at Divine Complexions. Whatever service you choose, you’ll leave feeling relaxed, rejuvenated and like a million bucks.

Canby Massage Co-Op (Canby)

Described by locals as a “healing oasis,” the Canby Massage Co-Op is your destination for relaxation. For skilled masseuses and a holistic wellness approach, the talented staff at Canby Massage Co-Op can do it all.

Three people playing a shooting arcade game

Trip Tips

Explore Oregon the Wilsonville way this summer. Plan your visit to cool off when there’s a fun summer event also going on in the region. Plan to stay the night (or weekend) and check out more itinerary inspiration. Don’t forget to pack your party pants!