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Chester Gap Cellars

4.3 (74 reviews)
ModerateWineries
Closed 11:00 am - 6:00 pm
Updated a few days ago

Chester Gap Cellars Photos

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Judy P.

Fabulous in every way. Extremely attentive service by Jeff, the views are absolutely stunning, breathtaking and spectacular, and the wines, especially if you purchase a flight provide so much variety and depth. You can really appreciate the minerality and climate here. We purchased a red, a white, and a rosé. There were so many choices and we wish we could've come home with much more but this just means we'll need to make a return visit soon. Absolutely worth the drive from DC and from anywhere. You will feel cared for and appreciated here and it's wonderful to support a small winemaker who also creates a welcoming environment!

View from tasting room deck.

I've visited Chester Gap Cellars twice - once in July and again in September. Each time, the staff were very friendly and knowledgeable about the wines. The quality of the wines were better than I expected for a Virginia winery. I particularly enjoyed the Rose and the Vintner's Red and bought a case to take home and share with friends, who also enjoyed the wines. The views from the tasting room and deck are simply beautiful. There was a food truck on-site during my recent visit and the winery sells/serves Charcuterie boards and other light bites to go along with the wine flight/tasting, wine by the glass, or bottle you purchase to enjoy while taking in the view. I look forward to returning and bringing friends with me.

Lauren G.

Amazing and breathtaking view! We both tried the wine flights and enjoyed them outside overlooking this amazing view! I can't wait to go here with my family when they visit me. Next time I'll try a wine slushie! My favorite wine was the lighter side of red. The service was fast and friendly. I can't get over how serene and remote the venue is. Another thing to mention is that they had a food truck as well on the Saturday when we went!

Frozen white wine
Nikita D.

Beautiful views, amazing staff, and great wine- Chester gap has it all! Loved our time at Chester gap with the beautiful scenic views of the mountains. The wine has good and affordable- I'd go with the wine flight as a great way to try all their offerings. They don't have a large food menu, mainly cheese boards and artisanal breads, but there was a food truck outside when we visited. We ordered the flight, frozen white wine, cheeseboard and stuffed cheese bread. My favorite from the flight was the rose, it was perfectly crisp and paired so well with the cheese and bread. The frozen wine is a great option if you like sweet drinks. This is a perfect place to relax, hang out with friends and enjoy the views.

Marin F.

best winery in front royal!! I live just minutes from this place and this has been my second time here. The wine for the prices are reasonable and very nice people who work there. I got a bottle of Riesling and their charcuterie board. So refreshing and just the perfect amount of food on a wonderfully sunny day. The pastrami was definitely the best part! Also, amazing views. Took my boyfriend's family here to see and they were breathtaken as well. overall, definitely come here to check out the amazing views while treating yourself to some wine!

Wine menu

Highly recommend! Kind hostess, great drinks, and amazing views. We all ordered the frozen white wines and loved it! The wonderful scenery and overlook added so much. When we went, there was a food truck there with very yummy salad and sandwiches. The winery also sells cheese and meat boards and stuffed artisanal breads (that smell like pizza)!

Dyonna B.

I visited this place with some friends this past weekend. I found them online and decided to visit their website. I loved that they mentioned on the site "All are Welcome" "We are proud to celebrate the diversity of all of our guest. No matter your gender, race, ethnicity, religion, ability or sexual orientation, we welcome you to our tasting room and vineyard. Celebrate what makes you unique now and always." I absolutely loved that they were inclusive and this is what makes a great business. Not to mention, service was great, the views were amazing and the wine was delicious. What more can you ask for? I would definitely visit this place again. We did the wine flights so we got a taste of 5 wines. There was a sweet wine that I really enjoyed that kinda had a tootsie roll taste to it. The rose' was a close second for me. Well done.

Rhonda W.

This winery was recommended to us by another couple at a wine tasting at Luray caverns (who had awful wine and did the tasting outside in the bitter cold). The couple said that Chesters Gap was wayyyy better so we looked them up. I totally agree .. much better experience.. highly recommend. wine was not cheap but reasonable. All the wine was good. the view is lovely but it was cold and rainy that day .. so too foggy to see the view.

View from Chester gap
Jonathan L.

Chester's gap is a nice spot to hang out and catch amazing views of the mountains. Chelsea is very kind and hospitable.

View from winery.
Ron C.

Amazing wine and amazing views. Extremely nice people. What a great place to come and relax. Take a nice stroll around the property with a fantastic glass of wine and snacks. This is a destination place.

Viet D.

Beautiful scenery and plenty of places to sit and enjoy! We had mulled wine, wine flight, cheese, salami and crackers and it was all good! Staff was very friendly! Our pup loved it too!

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Incredible service and atmosphere. Truly warm and inviting reception from the owner. Also superb service from staff.

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Review Highlights - Chester Gap Cellars

Chelsea greeted us upon arrival, made sure we had a beautiful place to sit and took our order for wine.

Mentioned in 5 reviews

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Crimson Lane Vineyards - Side porch

Crimson Lane Vineyards

(100 reviews)

We spent a few days in Fauquier County region and were able to check out some new wineries as well…read moreas a few favorite. Crimson Lane was one of the new spots and is now a favorite. Off the beaten track and up on hilltop with beautiful views, this winery is AMAZING! Tastings are table side with knowledge staff guiding you. They offer both their own estate wines as well as an assortment from VA and around the world. Their wines were well balanced with layers of flavor, depth and long finish. My favorites were the Petite Verdot and Sauvignon Blanc It is best to make a reservation. They also have a food menu. We did the 2 estate tastings, several glasses and shared a burrata. I could have stayed all day! My rating rationale for beer, wine, or spirits: +1 Service +1 Atmosphere/Vibe +1 Taste/Quality (Flavor, aroma, and overall quality of the beverage) +1 Presentation (Glassware, garnishes, and visual appeal of the drinks) +1 Selection/Variety (Range of beer, wine, or spirit options and uniqueness of offerings) My rating rationale +1 Service +1 Food~Taste/flavor/quality +1 Presentation +1 Atmosphere/vibe +1 Value

**I will preface this by the fact that for once in my life, I did not do my due diligence and…read moreresearch the wineries rules and regulations before coming. The review does not reflect the fact I did not get to try their wine, but rather the way I was treated when I attempted to plan a trip to visit the "right" way** We were driving past this spot on a nice Sunday, coming home from a family lunch, and thought why not stop in? I did not have a reservation because (as mentioned above) I wasn't aware of needing one and I wasnt sure when I would be able to stop in as I was just passing by (we live 1+ hour away). As we pulled into the long dirt road, the front gates have no clear sign that says 'By Appointment Only' - perhaps a good add before your clients drive up a steep unpaved road to just be turned away. None of the vines appeared to be in use so the drive up may be more beautiful one day when the grapes are on the vines. The parking lot is a bit cramped and full of fancy cars, giving us a taste of the type of clientele that would be inside. We came in and I inquired if I could do a wine tasting. The staff member told us we needed a reservation but that he would do his best to try to see if they had space - totally fine. My mistake again- I did not realize that this winery required reservations (no other winery I have been to in Charlottesville, Middleburg, or NOVA has done so) so my first assumption wasn't that I needed a reservation. Again, no sign at the front that says this and would have saved me time. The space was obviously gorgeous, the views spectacular and it felt very Napa and upscale. The staff member returned back and told us they couldn't accommodate us- ok, disappointing but ultimately is what it is. I asked the two staff members standing there how early they recommend making reservations, as we dont live in the area so I need to plan ahead. They told me it was hard to tell but that basically any time it's warm, it will be hard to get a reservation and that "Saturday visits are a pipe dream" and Sundays are "pretty impossible too". They then kindly told me "you could try to snag a reservation maybe a Thursday or Friday". Mind you, their hours are 12-5 on Thursday/Friday...I live an hour plus away, let alone with traffic. I guess my only options are to take off work to come visit as it seems there will be no chance for me to ever get a reservation for 2 on the weekends.... Needless to say, it felt like the staff really could care less for our future business and we politely left. The staff did not offer to help us book a future reservation or anything of that nature - just a snooty response that I probably shouldn't bother every attempting to return on a weekend. Hilarious enough, I decided to look up their website and low and behold - they had tasting reservations that same day at 3 PM (45 minutes after we first asked about a tasting) - no offer to us to wait or come back to return, just basically turned away. Cherry on top- they have tons of reservations open for future Saturdays and Sunday. If you don't want my business, you dont have to tell me twice. If I want to deal with pretentious folks, I'll fly to Napa and drink wine actually grown onsite.

Aspen Dale Winery at the Barn - Aspen Dale Winery--view from back

Aspen Dale Winery at the Barn

(227 reviews)

$$

CLOSED -- We believe this place is no longer open. We drove by and saw that the sign looked quite…read moreold, and the entrance appeared to be blocked off. Their website mentioned they are "mostly closed," and when we tried calling the listed phone number, it had been disconnected. The photos in previous reviews look great, so it was disappointing not to be able to visit.

This place is *chefs kiss* exquisite. If I were ever to write a novel I would want to write it…read morehere. I would imagine Thoreau would share my feelings. The outside of the barn is so quaint with ivys growing up the sides. Surrounding the area are another couple barns with mini donkeys and goats. Parking is plentiful. Be careful or you may miss the turn! Fortunately there is an OPEN sign showing you to your destination. The singer was an older gentleman with an amazing voice thick mustache resembling Sam Elliot's and plethora of string instruments. While sitting next to the fire pit, this sound mixed with the warm ambience is perfection. I opted for the sweets flight- one sweeter white, one rose, one sparkling cider and one sangria. Their homemade sangria tasted like raspberry lemonade. The flights come with tiny morsels of food pairings for each. The presentation is lovely and planned to perfection. They offer snacks and local favorites like apple cider donuts or farm fresh eggs from a neighboring farm. Up the winding staircase you will find a barn cat listening to strangers play chess and laugh amongst themselves. We played a game of checkers and enjoyed the warmth of the barn and the music echoing through the building. This place is magic- and is a Diamond in the rough. I can't wait to return.

Capstone Vineyards - Roussaine at sunset

Capstone Vineyards

(27 reviews)

Capstone Vineyards is a small family-owned vineyard and tasting room located on the slopes of Blue…read moreMountain. Friendly staff Interesting wines Beautiful views Comfortable tasting room What we tasted: notes directly from vineyards tasting menu. 2025 Sparkling Rosé: 100% Merlot, fermented and aged 5 months in steel Made sparkling with bulk CO2 Nose: orange blossom, strawberry, papaya Mouth: grapefruit, cantaloupe pomearanate 2024 C2 93% Chardonnay, 7% Chenin Blanc Aged 10 months in neutral French oak, made sparkling using the Charmat Method Nose: green melon, orange sherbet, candied almonds Mouth: marzipan, lemon drop, hibiscus 2025 Sparkling Chardonnay 100% Chardonnay. Fermented and aged 10 months in neutral French oak 30 months on the yeast. Champagne Method Nose: pear compote, shortbread, meringue Mouth: lemon curd, apple tart, Turkish apricot 2025 Sparkling Cider Made in the Acadian style, typified by bright acidity, crisp, clear, dry and sparkling Harrison, Arkansas Black, Black Twig, Goldrush and Winesap, Fermented and aged in tank, made sparkling with bulk Co2 Nose: green melon, hibiscus, cantelope Mouth: candied lemon peel, chamomile, sweet tarts 2025 Sauvignon Blanc 100% Sauvignon Blanc 70% fermented in tank, 30% fermented in neutral French oak Nose: croissant, honeycomb, cara cara orange, Mouth: lemon balm, nectarine, verbena tea 2024 Merlot 100% Merlot, aged 14 months in French oak (23% new oak, 77% neutral, Nose: anise, black cherry, balsam Mouth: blackberry, cola, candied strawberry 2024 Cabernet Franc 100% Cabernet Franc, aged 14 months in French oak (33% new oak, 67% neutral" Nose: nutmeg, lavender, black plum Mouth: tootsie roll, plum, leather Note we had to climb a steep stairway to tasting room. Im not sure if there is an ADA entrance My rating rationale for beer, wine, or spirits: +1 Service +1 Atmosphere/Vibe +1 Taste/Quality (Flavor, aroma, and overall quality of the beverage) +1 Presentation (Glassware, garnishes, and visual appeal of the drinks) +1 Selection/Variety (Range of beer, wine, or spirit options and uniqueness of offerings)

While visiting Crimson Lane Vineyards, we also stopped here. The tasting room was busy, with only…read moretwo staff members working, which resulted in inconsistent service. Although the staff were friendly and helpful, their divided attention noticeably impacted the overall experience. The venue offers attractive hilltop views; however, the tasting room itself is small and felt cramped even at half capacity. The wines were solid--slightly better than those at the neighboring vineyard--which aligns with the winemaker's established background and experience. The winery is family-friendly and allows children. Service was pleasant, and pricing was more reasonable than nearby options. I would consider returning with friends, bringing a picnic, and spending a relaxed afternoon outdoors while enjoying a few bottles.

Barrel Oak Winery & Brewery - Tasting room cheers

Barrel Oak Winery & Brewery

(691 reviews)

$$

We visited the winery on Valentine's Day, which fell on a Saturday this year. We had made a…read morereservation in advance and arrived a bit early, but were seated right away. Tables are reserved for 2.5 hours, so I assume the party before us didn't use their full time. We ordered an appetizer and a bottle of wine. The brie cake was delicious--even for someone who doesn't usually like goat cheese (it was layered in)--but unfortunately, no one in our group enjoyed the cheesecake. The winery is both dog- and kid-friendly. All the parents we encountered kept their children supervised, which is a winery rule and one I really appreciate now that we have kids ourselves. Most of the dogs were also very well behaved, though one was repeatedly growling at passing dogs, which was off-putting. While the winery can't control every patron, we choose to leave our dog at home when she's not in a social mood, and it would be nice if all dog owners did the same.

We came to celebrate my mom's birthday, and for our first visit, it was beautiful. They had a cute…read morefarmers market with small local shops. The live singer wasn't really my style, but others seemed to enjoy it. We did a wine flight, and our wine server (Nick) was super knowledgeable and helped us find what we liked. I even bought my mom a bottle to take home. It was a bit confusing at first, but the lady at the front was so kind and explained everything. There was plenty of seating, and we hung out upstairs in the lounge with a great view. The only thing I didn't love was the food--we got a charcuterie board, and I'm not sure I'd get it again. But overall the experience was still wonderful. Everyone was very nice, and we'll definitely be back! Also there's a cute kitty that lives on the property she's super friendly and sweet

Chester Gap Cellars - wineries - Updated May 2026

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