Deschutes Brewery
Deschutes Brewery started as a humble Bend brewpub and has grown into one of the largest craft breweries in the U.S. Their flagship pours, like Black Butte Porter and Mirror Pond Pale Ale, have earned a loyal following. Guests can sip in their tasting room with Deschutes River views, join free guided tours, and dig into a pub menu of burgers, pizzas, and seasonal bites. In 2025, the brewery is making a major push into non-alcoholic options, rolling out NA versions of Fresh Squeezed IPA and Black Butte Porter to tap into the rising health-minded beer trend.
5 minute drive, 13 minute walk, 0.5 miles from Pioneer Park Rentals
Address: 1044 NW Bond St, Bend, OR 97703
Phone: (541) 382-9242
Website: https://deschutesbrewery.com/
10 Barrel Brewing Company
Founded in Bend in 2006, 10 Barrel Brewing Company has grown from a local favorite to a national name, known for its hop-forward Cascadian IPAs and brewpubs in Portland, Boise, San Diego, and beyond. Now part of Anheuser-Busch (since 2014), its original Bend pub still anchors the brand’s identity, serving an extensive lineup of canned and draft beers that keep it woven into the city’s beer culture.
6 minute drive, 1.6 miles from Pioneer Park Rentals
Address: 1135 NW Galveston Ave, Bend, OR 97701
Phone: (541) 678-5228
Website: https://www.10barrel.com
Bend Brewing Company
Since 1995, Bend Brewing Company has been a downtown Bend staple, pouring award-winning beers brewed right on the banks of the Deschutes River. Its rotating tap list spans ales, IPAs, stouts, and seasonal creations, paired with a menu of elevated pub fare from hearty burgers to inventive small plates. A relaxed riverside patio—often shared by locals, visitors, and a few well-behaved dogs—sets the scene for casual hangouts, live music, and sunny afternoons.
4 minute drive / 14 minute walk, 0.9 miles from Pioneer Park Rentals
Address: 1019 NW Brooks St, Bend, OR 97701
Phone: (541) 383-1599
Website: https://www.bendbrewingco.com
Boneyard Beer
Opened in 2010 in a converted auto shop pieced together with salvaged gear from more than a dozen breweries, Boneyard quickly earned a following for its hop-forward ales with bold, clean flavors. Today, the Division Street pub offers a grand beer hall, wrap-around patio, and over 20 taps pouring fan-favorite brews.
2-minute drive / 10-minute walk, 0.4 miles from Pioneer Park Rentals
Address: 1955 NE Division St, Bend, OR 97701
Phone: (541) 241-7184
Silver Moon Brewing
Bend’s third-oldest brewery, Silver Moon opened in 2000 and blends small-town charm with a near-constant calendar of events — trivia, comedy, and open mics most nights of the week. Downtown on Greenwood Avenue, the taproom pairs its craft beers with rotating food trucks and a welcoming atmosphere.
4-minute drive / 13-minute walk, 0.6 miles from Pioneer Park Rentals
Address: 24 NW Greenwood Ave, Bend, OR 97703
Phone: (541) 388-8331
Website: https://www.silvermoonbrewing.com/
Bridge 99 Brewery
A little off the beaten path, Bridge 99 is a modest-sized brewpub with a big reputation. Known for inventive hop use and standout barrel-aged beers, it’s often called one of Bend’s best-kept beer secrets—valued for both its quality and its laid-back vibe.
7-minute drive, 2.8 miles from Pioneer Park Rentals
Address: 63063 Layton Ave, Bend, OR 97701
Phone: (541) 280-1690
Website: https://bridge99brewery.com/
Crux Fermentation Project
Launched in 2012 by a former Deschutes brewmaster, Crux is dedicated to pushing brewing boundaries—from hoppy pilsners and IPAs to sours, barrel-aged stouts, and even non-alcoholic creations. Perched on a small hill with Cascade Mountain views, its tasting room hosts “Sundowner Hour” timed with sunset, and rotating food trucks add to the lively, outdoor scene.
6-minute drive, 2.1 miles from Pioneer Park Rentals
Address: 50 SW Division St, Bend, OR 97702
Phone: (541) 385-3333
Website: https://www.cruxfermentation.com/
GoodLife Brewing Company
Founded in 2011, GoodLife crafts clean, balanced beers using Northwest hops, quality malts, and snowmelt from the Cascades. The Century Drive Bierhall and outdoor garden offer plenty of space to linger, often with live music or seasonal events like the Winter Beer Festival. The brewery shares the site with Back Drop Distillery, making it a two-for-one stop.
8-minute drive, 2.2 miles from Pioneer Park Rentals
Address: 70 SW Century Dr suite 100-464, Bend, OR 97702
Phone: (541) 728-0749
Website: https://www.goodlifebrewing.com/
Bledsoe Family Winery
Founded by former NFL quarterback Drew Bledsoe, this winery brings the rich, layered wines of Walla Walla to a chic Bend tasting room. Known for its bold reds and smooth blends, the winery’s modern space is perfect for lingering over a flight with friends or enjoying a quiet glass before dinner.
6 minutes, 2 miles from Pioneer Park Rentals
Address: 845 SW Columbia St, Bend, OR 97702
Website: https://bledsoefamilywinery.com/
Elixir Wine Group
Part international importer and part local tasting room, Elixir Wine Group curates a global selection alongside their own Oregon-made labels. Guests can sample varieties from across Europe and South America while learning the stories behind each bottle. It’s an ideal destination for adventurous wine drinkers who want to expand their palate beyond the Pacific Northwest.
6 minutes, 2 miles from Pioneer Park Rentals
Address: 11 NW Larch Ave, Bend, OR 97703
Website: https://elixirwinegroup.com/
Va Piano Vineyards – Bend Tasting Room
Bringing the flavors of Walla Walla wine country to Bend, Va Piano Vineyards offers a refined selection of cabernet sauvignons, syrahs, and sauvignon blancs. The tasting room’s comfortable seating and knowledgeable staff make it an excellent spot for both casual sippers and dedicated wine lovers. Its riverfront location means you can enjoy a glass while taking in one of Bend’s most picturesque settings.
9 minutes, 3 miles from Pioneer Park Rentals
Address: 425 SW Powerhouse Dr Suite 307, Bend, OR 97702
Website: https://vapinovineyards.com/
Crater Lake Spirits Tasting Room
Known for its handcrafted vodkas, gins, and whiskeys, Crater Lake Spirits has earned a loyal following for its smooth flavors and creative infusions. Visitors can try a flight of spirits, enjoy cocktail samples, and pick up a bottle to take home. The tasting room’s downtown location makes it easy to add to a day of exploring Bend.
15 minutes, 8.7 miles from Pioneer Park Rentals
Address: 19330 Pinehurst Rd, Bend, OR 97703
Phone: (541) 318-0200
Website: https://craterlakespirits.com/
Oregon Spirit Distillers
Oregon Spirit Distillers crafts award-winning whiskeys, gins, vodkas, and even absinthe, all made on-site in Bend. The spacious tasting room offers generous pours and guided tastings that give insight into the distilling process. It’s a welcoming spot for spirit enthusiasts and anyone curious about locally made, small-batch liquor.
6 minutes, 1.1 miles from Pioneer Park Rentals
Address: 740 NE 1st St, Bend, OR 97701
Website: https://oregonspiritdistillers.com/
