A beautiful old barn dating back to the days when Medford was all pear and fruit orchards.
1 / 11

RoxyAnn Winery Hillcrest Orchard

4.5
·212 reviews·Medford, United States

Historic barn winery with scenic views, offering wine tastings, tapas, and a relaxed country atmosphere. Family and pet-friendly.

Highlights

Highlights

Must-see attractions

Social content

Social

From TikTok & Reddit

Best Time

Weekday afternoons

Fewer crowds, more relaxed

CrowdLow
Loading map...
A beautiful old barn dating back to the days when Medford was all pear and fruit orchards.

RoxyAnn Winery Hillcrest Orchard

Best Time

Weekday afternoons

Fewer crowds, more relaxed

CrowdLow
Highlights

Highlights

Must-see attractions

Historic barn winery with scenic views, offering wine tastings, tapas, and a relaxed country atmosphere. Family and pet-friendly.

4.5
(212 reviews)

"Great atmosphere, great service, and parking is easy. PLUS... their wines are delicious."

Vertical photo
TIP

🚗 Easy Parking

Parking is generally straightforward and ample, making arrival hassle-free. 🚗

🐶 Pet-Friendly Patio

Bring your furry friends to enjoy the outdoor patio space with you. 🐕

Third hero image

Quick Facts

Hours

Rating

4.5 · 212 reviews

Type

Farm

♿ Wheelchair accessible🅿️ Accessible parking🚻 Accessible restroom

Highlights

Discover the most iconic attractions and experiences

Historic Barn Ambiance

Historic Barn Ambiance

Tasting Room

Experience wine tasting in a beautifully renovated historic barn, offering a unique and charming atmosphere.

Scenic Countryside Views

Scenic Countryside Views

Outdoor Seating Area

Enjoy your wine amidst bucolic country settings with expansive grassy areas perfect for relaxation.

Award-Winning Wines

Award-Winning Wines

Tasting Bar

Sample a variety of wines, with some visitors particularly praising the Petite Sirah and Viognier.

Your AI travel agent

Plans like a pro.
Thinks like you

Start Chatting

Planning Your Visit

Timing is Everything

Avoid weekend crowds by visiting on a weekday. Consider arriving earlier in the day to enjoy the serene atmosphere before it gets busy. Some visitors suggest weekdays offer a more relaxed experience.

Wine & Food Experience

While known for wine, food options can be limited. Be prepared for self-serve charcuterie or food carts. Confirm kitchen availability if a full meal is desired.

Best Times

When
Weekday afternoons
Why
Fewer crowds, more relaxed
Crowd
Low
When
Late Spring/Early Fall
Why
Pleasant weather for outdoors
Crowd
Medium

Insider Tips

from TikTok, Instagram & Reddit

reddit.com

Looking to visit Medford. Any recommendations or must-do’s when in town?

Really depends on the season as everyone is saying. To be specific to Medford: Roxy Ann peak is cool! And so are hiking the table rocks. The farmers market is really nice on Thursdays when it’s in season. I also really like Padigan winery. Good views, wine, and food. Ruby’s is…

🚗 Easy Parking

Parking is generally straightforward and ample, making arrival hassle-free. 🚗

🐶 Pet-Friendly Patio

Bring your furry friends to enjoy the outdoor patio space with you. 🐕

reddit.com

24 Hours in Medford

Arriving in 2 weeks. Visiting Medford for the first time. Business trip. First two days I drive north for business. Last 24 hours in Medford for fun. What would you do if you were me?

reddit.com

Southern Oregon winery recommendations?

Looking to spend a day tasting there this fall. Love to hear about any can't miss wines/wineries - also open to tips for restaurants, accommodations, etc. Cheers!

🧀 Self-Serve Snacks

Prepare for self-serve charcuterie or food carts; bring your own knife for baguettes if needed. :baguette_bread:

🍷 Wine Quality Varies

Palates differ; some find wines over-oaked, others praise specific varietals. :wine_glass:

reddit.com

Recommendations for visitors

We’re from the Midwest, flying into Medford today and visiting Jedediah Smith Woods tomorrow. I’ll stay in Gold Beach for a couple days, then back to Medford on Thursday to fly home Friday. Any good recommendations for super easy hikes with nice views, live music, museums, cool…

Tips

from all over the internet

🚗 Easy Parking

Parking is generally straightforward and ample, making arrival hassle-free. 🚗

🐶 Pet-Friendly Patio

Bring your furry friends to enjoy the outdoor patio space with you. 🐕

🧀 Self-Serve Snacks

Prepare for self-serve charcuterie or food carts; bring your own knife for baguettes if needed. :baguette_bread:

🍷 Wine Quality Varies

Palates differ; some find wines over-oaked, others praise specific varietals. :wine_glass:

👨‍👩‍👧‍👦 Family Welcome

Kids are welcome, and there's space to roam, making it suitable for family outings. :child:

What Travellers Say

4.5
(212 reviews)

Reviews Summary

RoxyAnn Winery offers a unique experience with its historic barn and scenic country setting, often praised for its welcoming atmosphere for families and pets. However, opinions on wine quality and service can be divided, with some visitors finding the wines over-oaked and service inconsistent, while others appreciate the generous pours and specific varietals. The self-serve food options add to its rustic charm but may not suit everyone's expectations for a full dining experience.

"I made a reservation for 10 in March, confirmed it the day before coming, and when we showed up 10 min early the guy in a t-shirt behind the bar said weren't in the books. While that ended up not being an issue (they were empty), it was not a great start.

The pours were enormous but the wine was bad. They had shuffleboard, board games, food carts, and a coffee shop. The old barn was the best part of the visit.

I know palates differ, but the wines were over oaked, heavy handed, and low quality. I dumped most of each tasting, as did many in my group. The unanimous least favorite wine tasting of the 6 we visited in the Rougue Valley / Applegate Valley."

Steven Melhorn

"What can I say about RoxyAnn that you don't already know. Great atmosphere, great service, and parking is easy. PLUS... their wines are delicious. The petite syrah is definitely my favorite!!! I love the history of the property and the fact that you can take your dogs and kids and enjoy wine and the world's best blue cheese (by Rogue Creamery) under the covered patio. The big grass area is a plus for us especially when the sun is out. Being a party rental company who runs our business out of our home office, I wasn't sure where to host my Grand Opening ribbon cutting ceremony and RoxyAnn was the perfect spot for us to celebrate. They were so accommodating! Thank you so much to the staff for always making us feel important and comfortable. Great wines and great staff."

Carrie Garcia-McPheeters

"My husband and I drove 2 hours out of the way to try their wine. We are from out of state and we were on a road trip. After reading the reviews, I suggested this winery for a nice relaxing tasting. Once we arrived were were notified that it was self-served. Okay, interesting. We were starving and wanted a beautiful meal with nice wine. We were notified that they do not have a kitchen but serve cold cuts and cheese. We bought some Gouda, whole baguette, and a spread. To my surprise, we had to cut the hard baguette on our own and the cheese with a plastic knife. After struggling to cut the bread. I asked, if I could have a better knife to cut it. It was provided. The bread was too hard to eat so I asked if it was possible to warm it up. It was tossed in a toaster and I had to get out. All in all, this was a different tasting. Having paper plates and plastic knives to cut your own bread is not ideal. My husband and I did not like any of the 5 wines we tried, which added to the burn. The staff asked us how was the wine. We told them we didn’t like any of them. They didn’t offer any additional recommendations.

We realized, if we rushed out of RoxyAnn — we could make it to a different winery. So we paid and left as soon as possible. I’m glad we did."

Kimberly Orellana

What People Like

Historic barn ambiance
Pet and family-friendly
Scenic country views

What People Dislike

Inconsistent wine quality
Variable service experiences
Self-serve food limitations

Frequently Asked Questions

🚇 🗺️ Getting There

RoxyAnn Winery is located in a country setting outside of Medford. Driving is the primary mode of transport. Visitors often mention it's worth a detour for the experience. Reddit

Yes, parking is generally easy and plentiful at the winery, making it convenient for visitors arriving by car. Reddit

RoxyAnn Hill is mentioned as a hiking spot, suggesting the winery is situated in an area with outdoor recreational opportunities. Reddit

🎫 🎫 Tickets & Entry

Reservations are recommended, especially for larger groups, though walk-ins may be accommodated if the winery isn't busy. One visitor noted a reservation issue, so confirming is wise. Reddit

Opening hours can vary, but it's often open on weekdays and weekends. It's best to check their official website or social media for the most current hours before your visit. Reddit

Typically, there isn't an entrance fee to visit the grounds, but wine tastings and food purchases will incur costs. Reddit

Yes, dogs are welcome on the patio and grounds, making it a great spot for pet owners to enjoy a tasting. Reddit

Absolutely, children are welcome at RoxyAnn Winery. The spacious grounds offer room for them to explore while adults enjoy their wine. Reddit

🍽️ 🍽️ Food & Dining

RoxyAnn Winery does not have a full kitchen. They typically offer self-serve charcuterie boards, cheese, and baguettes, or have food carts available. Reddit

Expect options like cheese, cold cuts, and baguettes. Some visitors have noted you might need to cut your own bread, so be prepared for a rustic experience. Reddit

While they offer food, it's generally best to check their policy on outside food. However, the focus is on enjoying their wine with their provided snacks. Reddit

Cheese and baguette options are usually available, which can cater to vegetarians. Confirm with staff upon arrival for specific offerings. Reddit

Some reviews mention a coffee shop on-site, adding another amenity for visitors to enjoy alongside wine and snacks. Reddit

🎫 🍷 Wine & Tastings

The tasting experience can be self-served or guided. Pours are often generous. However, wine quality is subjective; some find it over-oaked, while others praise specific varietals like Petite Sirah and Viognier. Reddit

Tasting fees can apply, and some visitors have noted being charged for additional tastes. It's advisable to inquire about tasting costs and policies beforehand. Reddit

Visitors have specifically recommended the Petite Sirah and Viognier. The Malbec and other reds have also received positive mentions. Reddit

Yes, you can purchase wine by the glass to enjoy on-site or by the bottle to take home. Reddit

While not explicitly detailed in all reviews, many wineries in the region offer wine clubs. It's worth inquiring directly if you're interested. Reddit

📸 📸 Photography

The historic barn, the expansive grassy areas, and the scenic countryside views offer excellent photo opportunities. Capture the rustic charm and the bucolic setting. Reddit

The picturesque setting with the barn and rolling hills makes it a potentially beautiful backdrop for engagement or wedding photos. Reddit

You may also like

RoxyAnn Winery Hillcrest Orchard (2026) – Best of TikTok, Instagram & Reddit Travel Guide