It’s Wine o’Clock Somewhere

Bend may be Beer Town, USA, but the city also boasts a passionate wine crowd. Bend has about a dozen wine bars and tasting rooms, which doesn’t include restaurants. While a glass of wine has always been more expensive than a mug of beer, it is possible to find some deals during happy hour. And some wine bars even have entire happy days!

Flights Wine Bar

What’s better than Happy Hour all day? Flights Wine Bar on NW College Way offers $2 off any glass of wine daily from 3-5pm and all day on Wednesdays. Flights features wines from all around the world.

“Each week we do a new flight and all of those are available by the glass,” owner Kelsey Daniels told the Source. Flights offers five flights and about 20 different wines by the glass.

wine bottles on a table — On Wednesdays, Flights offers $2 off any glass of wine all day. Credit: Nic Moye

exterior of Flights Wine Bar — Flights Wine Bar won the 2025 Wine Spectator Restaurant Award of Excellence. Credit: Nic Moye

Daniels takes care in selecting the wine. “I look for smaller productions, family owned, if possible. At least not owned by a giant company. We look for wineries that are practicing sustainability, organic, land stewardship programs we like to support and just good quality for the price. So if you get the $12 glass, it’s going to be a good glass for $12, and if you get the $25 glass, it’s going to be a really good wine for $25.” Daniels says she has felt the impact of recent tariffs on prices.

Flights’ Happy Hour menu has 10 discounted food items as well, including seasonal soup, salads, fried calamari and smoked crab dip.

The wine bar, which opened in 2021, won Best Wine Bar of Central Oregon 2025 in the Source and recently received the 2025 Wine Spectator Restaurant Award of Excellence.

Other venues in Bend also offer $2 off wine deals during Happy Hour including Roam in the Oxford Hotel and Lady Bird in the Old Mill District.

Flights Wine Bar

Happy Hour daily 3-5pm and Wed 3-9pm

1444 NW College Way, Bend

flightswinebend.com/

$2 off wine deals

Roam

Happy Hour daily 2-5pm & 9-10pm

10 NW Minnesota Ave., Bend

roambend.com/

$2 off wine deals

Lady Bird

Happy Hour daily 3-5pm

375 SW Powerhouse Dr., Unit 130, Bend

ladybirdbend.com/

$2 off wine deals

Portello Lounge

In Northwest Crossing, Portello Lounge, which was runner-up for Best Wine Bar in Central Oregon in our 2025 readers’ poll, offers Happy Hour Tuesday through Saturday with $7 Happy white, red or bubbles options. Every Monday, all of the wines are $9 a glass with 20 different wines listed on the menu.

The recently updated food menu has a Happy Bites menu with nearly a dozen items including Moroccan roasted carrots, street corn dip and meatballs Pomodoro offered Tuesday through Saturday.

Portello Lounge

Happy Hour Tue-Fri 5-6pm, Sat 2-5pm

2754 NW Crossing Dr., Bend

portellobend.com/

Mondays $9/HH $7 wine deals

Austin Mercantile

woman behind food counter — Sara Hammond recently became the new owner of Austin Mercantile. Credit: Nic Moye

Austin Mercantile is a coffee/wine bar doubling as a home décor/gift shop in Brookswood Plaza in SW Bend. While it caters to almost any taste, wine is front and center with Happy Hour daily from 4-6pm, with selected red or white wine $9 a glass. On Wednesday wine nights from 4-8pm, all wines are $9 a glass.

Now under new ownership, Sara Hammond says she will change the wine selection seasonally. “I’m going to be switching that up at the end of September and trying to find wines that people are going to be having more for holiday dinners or parties. I am going to have a select few that I’m going to keep that are really popular. Kind of a staple.” Hammond was in the wine business for a decade before purchasing Austin Mercantile.

The food menu has also been revamped, offering bruschetta, meatballs, caprese salad and appetizers. The art and much of the home décor sold in the store are from local artists.

Austin Mercantile

Happy Hour Tue-Sat 4-6pm

19570 Amber Meadow Dr., Bend

austinmerc.com/

$9 wine deals

Pine Tavern

Built in 1936, Pine Tavern in downtown Bend has one of the best Happy Hour wine deals in town. Offered only in the bar, customers can order a glass of Happy Hour red or white wine for $6. A food menu with several options is available for $10, $11 or $16. Pine Tavern was runner-up for Best Happy Hour in Central Oregon in 2025. The iconic restaurant has stood the test of time in one of the most scenic locations on Mirror Pond.

Pine Tavern

Happy Hour Tue-Fri 2-5pm

967 NW Brooks St., Bend

pinetavern.com/index.html

$6 wine deals

Pastini

Pastini may be a chain restaurant, but you can’t beat half-price bottles of wine every Wednesday. The pasta palace located in the Old Mill District features local vintages from Oregon and Washington to wines from Italy. That’s 50% off any bottle. Just sayin’.

Pastini

Wine Wednesdays 11am-9pm

375 SW Powerhouse Dr. #3436, Bend

pastini.com/

50% off all wine bottles

Other Happy Hour Wine Deals

Salute

Happy Hour Wed-Mon 4-5pm

1045 NW Bond St., Bend

salutebend.com/happy-hour-menu

$3 Off Glasses of Wine

Feast