If your next trip to Walla Walla includes a visit to the pretty Southside tasting district, consider a stop at one of the latest tasting rooms to open in the area. Here are a few for your itinerary.
Bledsoe Family Winery: Quietly opened July 30th, the Bledsoe brand continues its steady expansion with the relocation of its downtown tasting boutique to a sprawling, custom-built facility, perched in the winery’s estate vineyard on Peppers Bridge Road.
“Moving our tasting experience to the Southside of the Walla Walla Valley is an exciting milestone for Bledsoe Family Winery,” said Josh McDaniels, CEO and Director of Winemaking and Partner of Bledsoe Wine Estates. Both McDaniels and his business partner, former NFL quarterback Drew Bledsoe, were raised in Walla Walla, and when considering a larger, more accommodating tasting room, it was important to remain local. “It brings our guests closer to the vineyards, the growers, and the agricultural heritage that shape every bottle we make,” McDaniels said.
This new tasting room, distinct from the Bledsoe/McDaniels property on the Eastside, and premium cabernet house, Doubleback, also on the Southside, offers expansive views of the Blue Mountains, indoor and outdoor seating, and Bledsoe Family Winery’s latest wines. These include the newly released 2024 Estate Red made from 100% estate cabernet, and a forthcoming sparkling wine. While on site, don’t forget to join the waitlist for yet another Bledsoe/McDaniels venture: olive oil from Bledsoe|McDaniels Olive Mill.
3599 Peppers Bridge Road | 509-792-3510 | 11am-5pm, Wednesday-Saturday; 10am-4pm, Sunday. Walk-ins welcome.
Everen: Opened in July 2025, Everen means “Every Season.” The idea that every season offers something fresh and renewed is what winemaker Matt Askel, and his business partner and fiancée, Hope Trumbull, intend to express through their design-focused and hospitality-driven winery.
Located on its 3.5 acre estate vineyard, guests enter a minimalist structure with clean lines and soaring windows offering panoramic views of the area. Crafted from wood, stone, glass, and metal materials, the focus is as much on creating an inviting and calm place to relax and unwind as it is wine.
Rotating flights of limited production still white and red wines, including varieties such as chardonnay, viognier, and syrah, are offered throughout the year, allowing the owners, the website notes, “to make a broad range of varieties and styles [that allow] us to pair wines with what’s fresh throughout the year.”
When it comes to food, wine club members can reserve a “Seasonal Table” tasting, a private 4-5 course food and wine tasting experience hosted after hours at the tasting room.
“It’s a place built for connecting with friends over good wine (or beer) and enjoying the rhythms of each season in Walla Walla,” the website states.
1823 Old Milton Hwy | 971-219-7170 | By reservation Monday-Wednesday. 10:30am-4pm, Thursday-Sunday. Reservations encouraged, walk-ins subject to availability.
Five Dollar Ranch: In May, locals rejoiced when this beloved microbrewery supersized its digs and relocated from its original locale—brewer Josh Hulett’s converted home garage, shared with his ever-patient wife, Susan—to a much-larger and more accommodating tap house on an expansive property. Now there’s room for everyone, kids and dogs (under supervision) included.
An always-changing selection of beers, including the popular Goat Candy IPA, along with various lagers, ales, and stouts, keep thirsty patrons happy. Food trucks, an outdoor patio, and a regular rotation of visiting adoptable dogs from the Humane Society (Josh and Susan are big animal lovers) add to the convivial atmosphere steadily made up of regulars and tourists. Unobstructed views of the Blue Mountains, so called for the bluish hue they cast when seen from a distance, make for a postcard (or Instagram) worthy backdrop.
Such a temple to beer is a perfect addition to the district, chock-a-block with world-class wineries. Consider renting a southside Air BnB or finding a nearby Harvest Host to make the most of the setting and keep all the new, expanded offerings within a stone’s throw.
3557 Peppers Bridge Road | 509-540-3989 | 2-7pm, Monday, Wednesday, Thursday; 2-8pm, Friday; 12-8pm, Saturday; 12-7pm, Sunday.
Floating Balance: Rounding out the latest additions to the Southside is this boutique winery, which opened its permanent tasting room, two cleverly upcycled shipping containers, in July 2025.
In 2020, owners David Kreindel and Shane Erickson bought a vineyard, named Aria, that was originally part of Pheasant Run Vineyards. The two never thought they would make wine, intending instead to lease the acreage. But then COVID happened, which upended business as usual—and their plans.
By 2023, Kreindel and Erickson had launched their own winery, establishing Aria as the estate vineyard of Floating Balance—named for a mechanism in watches and clocks, a passion of Erickson’s. The winery produces a number of white wines, including a rosé and sauvignon blanc, as well as red wines and an estate cabernet. The colorful, expressionist artwork featured on their wine labels is created by local artist, Frankie Laufer.
Like many small wineries in Walla Walla, Kreindel says it’s a micro production operation, but ultimately a true “labor of love.”
“We only make 400 cases a year. When we run out, we run out!”
2100 Stateline Road | 509-520-3869 | Wednesday-Thursday by appointment. 11am-4pm, Friday-Sunday.