Jessie’s Grove Winery sits on land that’s been growing grapes since 1888, and you can still walk among some of those original vines when you visit with your leashed dog. The property centers on a weathered barn and grove of massive oak trees that gave the winery its name—it’s named after the daughter of the original farmer, which adds real character to the place.

The grounds are genuinely walkable. You and your dog can spend time under the oaks, which provide good shade on warm days. There’s a small museum area with artifacts and interpretive panels explaining the land’s history before vineyards took over, so it’s worth reading through while you’re there. The spot works well for a picnic if you bring your own food and want to sit with your dog nearby.

Jessie’s Grove hosts a summer concert series that draws crowds, and during those events dogs typically aren’t welcome—worth calling ahead if you’re thinking about timing your visit around a performance. But on regular days when there’s no event happening, it’s a relaxed place to spend a few hours. The winery produces wines from their old-vine stock, so you’re tasting something with actual depth of history behind it.

The setting feels more like a working farmstead than a polished resort winery, which means it has a genuine quality without being fussy. Bring water for your dog since you’ll be walking around, and note that while the grounds are dog-friendly, you’ll need to keep your dog on leash the entire time. If you’re planning to come during their summer concert season or any special event, call to confirm that dogs are allowed that particular day.