Trails

Self-Guided Hiking on Sundays

We welcome you to hike our beautiful estate on Sundays and holidays during the spring and summer to enjoy the sights, sounds, and smells while walking through our growing vineyard.

The trails are open Sundays from 11 am - 3pm. 

We have two trails that can be hiked separately or combined for a longer loop:

- Boot Loop (~1 mile): Starting near the top of the Tasting Room parking lot, this trail is relatively flat and stretches down to our Boot block where you get an expansive look up at the vineyard. Return to the winery and Tasting Room or cross the driveway and head up the Windmill Hill. 

- Windmill Hill (~3/4 mile): Starting on the east side of the overflow parking lot, this trail starts out with a steep climb to the top of the hill. Make your way around to the windmill for a view of the valley below and then head back down the hillside to the winery and Tasting Room, or cross the driveway and head down to the Boot Loop. 

Please check in at the Tasting Room to collect your map and let our staff know you’re here. Make your reservation for a wine tasting or to enjoy a glass of wine after your hike - Reserve Here On Tock!

Pets are allowed on the hike but must be cleaned up after and on a leash at all times. We appreciate you respecting our vineyard and our vineyard workers. 

Upcoming Events

Riesling Curious?

Mar 12, 2026 - Mar 14, 2026

Riesling Day | March 12–14 Are you a little Riesling curious? Join us as we celebrate this beautifully versatile grape with a special tasting opportunity in the Tasting Room. All flights will include ... read  more

Riesling Day | March 12–14 Are you a little Riesling curious? Join us as we celebrate this beautifully versatile grape with a special tasting opportunity in the Tasting Room. All flights will include two bonus pours—our 2024 Riesling (dry) and 2016 Riesling (off-dry)—served side by side so you can explore how style and time shape this expressive varietal. To continue the ...

Spring Wine Club Pick Up Party

Mar 15, 2026

Calling All Wine Club Members! Join us for our Spring Wine Club Party to taste our latest releases and pick up your allotment.  The 2019 Pinot Noir Reserve will be making its debut for you, ... read  more

Calling All Wine Club Members! Join us for our Spring Wine Club Party to taste our latest releases and pick up your allotment.  The 2019 Pinot Noir Reserve will be making its debut for you, and we'll be pouring the 2017 and 2018 Pinot Noir Reserves alongside it for a vertical trio tasting.  Plus, sneak into the cellar and get a peek (and a taste) of the wines we are showcasing ...

Founders Club Party

Apr 11, 2026

The Annual Founders Club Event is back, and we’re thrilled to welcome Marisa and Erin from Mack & Cheese to join us for the occasion. Together, we’ll explore pairings between our ... read  more

The Annual Founders Club Event is back, and we’re thrilled to welcome Marisa and Erin from Mack & Cheese to join us for the occasion. Together, we’ll explore pairings between our newest wine releases and a selection of seasonal cheeses.  As a member of the Founders Wine Club, this is your opportunity to taste through the lineup and hand-select the perfect 12 bottles to ...

Winemaker Dinner at Steamboat Inn

Apr 25, 2026

For more than 20 years the best chefs, winemakers, brewers, and distillers from around Oregon have joined forces at Steamboat Inn to create special nights of food, drink, and friendship. The intimate ... read  more

For more than 20 years the best chefs, winemakers, brewers, and distillers from around Oregon have joined forces at Steamboat Inn to create special nights of food, drink, and friendship. The intimate and magical surroundings of Steamboat Inn lead to amazing collaborations that diners would not be able to experience in a traditional restaurant or tasting room setting. Join Head Winemaker, Ariel ...

Pinot Blanc Oregon

May 3, 2026

Oregon has recently become the largest producer of Pinot Blanc in North America and we continue to gain critical acclaim for the selections of wine made here. Join us for a day of discovery ... read  more

Oregon has recently become the largest producer of Pinot Blanc in North America and we continue to gain critical acclaim for the selections of wine made here. Join us for a day of discovery and tasting with 12+Willamette Valley Pinot Blanc producers at Winter's Hill.  Each has a unique winemaking story to tell and an expressive wine to share.   Learn More & Buy Tickets
Winter's Hill
Winter's Hill 97114 6451 NE Hilltop Lane, Dayton, OR 97114
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