Chestnut Hill Winery
1 / 10

Chestnut Hill Winery

4.7
·197 reviews·Crossville, United States

Discover award-winning wines, unique gifts, and friendly service at Chestnut Hill Winery, a delightful stop off I-40.

Highlights

Highlights

Must-see attractions

Social content

Social

From TikTok & Reddit

Best Time

Weekdays, afternoons

Fewer crowds, more personal attention

CrowdLow
Loading map...
Chestnut Hill Winery

Chestnut Hill Winery

Best Time

Weekdays, afternoons

Fewer crowds, more personal attention

CrowdLow
Highlights

Highlights

Must-see attractions

Discover award-winning wines, unique gifts, and friendly service at Chestnut Hill Winery, a delightful stop off I-40.

4.7
(197 reviews)

"The wines are delicious and the tasting was fun! The gentleman who served us was very knowledgeable and super friendly."

Vertical photo
TIP

🎯 Try the Blackberry Wine

Don't miss their award-winning Blackberry wine – it's a local favorite!

🍫 Dessert Wine Delight

The Chocolate Covered Cherry wine is a must-try for a sweet, dessert-like experience.

Third hero image

Quick Facts

Hours

Rating

4.7 · 197 reviews

Type

Farm

♿ Wheelchair accessible🅿️ Accessible parking

Highlights

Discover the most iconic attractions and experiences

Award-Winning Blackberry Wine

Award-Winning Blackberry Wine

Savor the rich, award-winning Blackberry wine, a local favorite that's a must-try for any visitor.

Chocolate Covered Cherry Wine

Chocolate Covered Cherry Wine

Indulge in this unique dessert wine, a delightful blend of cherry and chocolate with a sweet finish.

Unique Gift Shop Finds

Unique Gift Shop Finds

Explore a treasure trove of local and wine-related items, perfect for gifts or souvenirs.

Your AI travel agent

Plans like a pro.
Thinks like you

Start Chatting

Planning Your Visit

Plan Your Visit to Chestnut Hill Winery

Discover award-winning wines and unique gifts at Chestnut Hill Winery. Enjoy daily tastings and educational tours. Perfect for a relaxing stop off I-40.

What to Expect at Chestnut Hill Winery

Experience friendly service and delicious wines, especially their Chocolate Covered Cherry and Muscadine. The gift shop offers unique finds for wine lovers.

Best Times

When
Weekdays, afternoons
Why
Fewer crowds, more personal attention
Crowd
Low
When
Weekends, late morning
Why
Lively atmosphere, good for groups
Crowd
Medium

Insider Tips

from TikTok, Instagram & Reddit

Pinot Gris headed to the winery from Chestnut Hill Vineyard.
lemelsonwinery
69 likes • 620 views

🎯 Try the Blackberry Wine

Don't miss their award-winning Blackberry wine – it's a local favorite! Instagram

🍫 Dessert Wine Delight

The Chocolate Covered Cherry wine is a must-try for a sweet, dessert-like experience. Reddit

Welcome to the Cumberland County, one of fourteen counties in the Upper Cumberland region. ✨ When visiting Cumberland County, Chestnut Hill Winery is a must. Make sure you visit with Jim and try their award winning Blackberry wine! 🍷 You can also grab a quick lunch at the Brass Lantern located next to the winery. You won’t be disappointed! Add some of the incredible outdoor magic this region has...
uppercumberland_tn
37 likes • 533 views
Add wine tasting at @chestnuthillwinery to your travel itineary in the Sequatchie Valley🍷 Visit our website at the link in our bio for more recommendations on where to eat and drink in the valley! #sequatchievalley #sequatchievalleytn #scenicbyway #crossville #chestnuthillwinery #crossvilletn #localwinery
sequatchievalleytenn
6 likes • 454 views

🛍️ Unique Gift Shop

The gift shop has fantastic, unique items for wine enthusiasts and more. Reddit

🗣️ Friendly & Knowledgeable Staff

Expect super friendly and knowledgeable staff eager to share their process. Reddit

🍷 Ever noticed the streaks (or legs) in your glass after a swirl? In this glass of Southern Muscadine from @chestnuthillwinery. The legs are thick but move quickly. That’s often a sign of a sweet wine with a little extra sugar and a bit lower alcohol content. 🍇 It’s a fun clue for wine lovers and a perfect way to enjoy a rich, flavorful sip of Tennessee sweetness. 💜 #TennesseeWine #Wine101 #Mus...
tennesseewines
7 likes • 516 views

Tips

from all over the internet

🎯 Try the Blackberry Wine

Don't miss their award-winning Blackberry wine – it's a local favorite! Instagram

🍫 Dessert Wine Delight

The Chocolate Covered Cherry wine is a must-try for a sweet, dessert-like experience. Reddit

🛍️ Unique Gift Shop

The gift shop has fantastic, unique items for wine enthusiasts and more. Reddit

🗣️ Friendly & Knowledgeable Staff

Expect super friendly and knowledgeable staff eager to share their process. Reddit

🚗 Easy Stop Off I-40

Conveniently located right off I-40, making it a perfect stop. Reddit

What Travellers Say

4.7
(197 reviews)

Reviews Summary

Visitors rave about Chestnut Hill Winery's delicious and unique wines, especially the Chocolate Covered Cherry and Blackberry varieties. The friendly and knowledgeable staff, along with the charming gift shop, create a welcoming and memorable experience. While primarily a wine destination, its convenient location and pleasant atmosphere make it a worthwhile stop.

"20240930 Their Chocolate Covered Cherry Wine is even better than the bottle I got in AL!! 😋 This wine is kind of like dessert wine, very sweet. It's cherry wine with a hint of chocolate toward the end. I can smell the cherry and chocolate. Very nice. I think my friends and family will enjoy it. The lady was so nice! So glad I found this winery on Google Maps last night."

Tilly Lo

"The wines are delicious and the tasting was fun! The gentleman who served us was very knowledgeable and super friendly. It’s a nice place to stop in and enjoy."

Sonya Abrams

"Really enjoyed our stop at Chestnut Hill Winery yesterday and meeting Trudi at this precious winery right off 40! We really enjoyed the wine and the shop was especially cool with great gifts for wine enthusiasts or just plain fun.

I will definitely be coming back and bringing a group

#wine #tennesseewine #cumberlandwinecountry

Take a look at my PHOTOS not all listed in the REVIEW"

Travel with Wendy

What People Like

Delicious, unique wines
Friendly, knowledgeable staff
Charming gift shop

What People Dislike

Limited public transport

Frequently Asked Questions

🚇 🗺️ Getting There

Chestnut Hill Winery is conveniently located right off I-40, making it an easy stop for travelers. Reddit It's situated in Cumberland County, part of the Upper Cumberland region of Tennessee. Instagram

Public transport options are limited in this region. It's best to travel by car to reach Chestnut Hill Winery. Consider ride-sharing services if available in the area.

The winery is located in Crossville, Tennessee. Nearby larger cities include Knoxville, which is about an hour and a half drive away.

Yes, the winery is located in the Sequatchie Valley, known for its scenic beauty. You can also find dining options like The Brass Lantern nearby. Instagram+1

Absolutely! The winery is a great stop along the Sequatchie Valley scenic byway, offering beautiful views and local charm. Instagram

🎫 🎫 Tickets & Entry

Entry to the winery is generally free, and they offer free tastings on 3 wines. Reddit Additional tastings or specific wine experiences may have a fee.

The winery typically offers daily tastings and is open throughout the day. It's always a good idea to check their official website or social media for the most current hours before your visit.

While not explicitly stated, it's common for wineries to accommodate group bookings or private tours. Contacting them directly in advance is recommended to arrange such experiences.

No, there is no admission fee to browse or shop in the gift shop. You can explore their selection of local and wine-related items freely.

Yes, as with all wineries, you must be of legal drinking age (21 years or older) to participate in wine tastings.

🎫 🍷 Wine & Tasting

Chestnut Hill Winery offers a variety of wines, including their popular Blackberry wine, Chocolate Covered Cherry wine, Southern Muscadine, and Hillbilly Shine Wine. InstagramReddit

The streaks or 'legs' in a wine glass after swirling are often an indicator of sweetness and alcohol content. Thicker, slower legs can suggest a sweeter wine with more sugar and potentially lower alcohol. Instagram

Yes, Chestnut Hill Winery offers tastings, with free tastings available on 3 wines. Reddit This is a great way to sample their offerings before making a purchase.

Many of the popular wines, like the Chocolate Covered Cherry and Blackberry, are described as sweet or dessert-like. Reddit They also offer varieties like Muscadine, which can vary in sweetness.

The winery features educational tours where the owner may gladly explain their winemaking process. Reddit It's a great opportunity to learn about how their fine wines are made.

🎫 🛍️ Shopping & Gifts

The gift shop is filled with cool, unique items, including local crafts and wine-related merchandise, perfect for wine enthusiasts or as fun gifts. Reddit

Reviews suggest good prices, especially on their sweet wines and the unique items in the shop. Reddit

Information about online wine sales is not readily available. It's best to visit the winery in person to purchase their wines or inquire directly about online ordering options.

Given the focus on wine-related items, it's highly likely they sell wine accessories such as corkscrews, stoppers, and glassware in their gift shop.

Yes, the gift shop features local items, reflecting a piece of southern pride that the owners are proud to share with customers. Reddit

You may also like

1 of 2
Chestnut Hill Winery (2026) – Best of TikTok, Instagram & Reddit Travel Guide