Hilton Garden Inn Lenox Pittsfield

08/31/2026

🍷🍂 **Sip, Savor & Celebrate in Lenox!** 🍂🍷

Wine lovers, here’s a delicious reason to plan a September getaway to the Berkshires! The **Lenox Wine Festival** returns for its fourth year on **Saturday, September 19th** at **The Barn at Pizzeria Boema** in Lenox.

Spend the afternoon discovering wines from around the world with **unlimited tastings**, meet passionate wine experts, importers and producers, and even shop featured bottles at special festival pricing. And it’s not just about wine — guests can also sample **local craft beer and cider** and enjoy tasty offerings available for purchase, including **wood-fired pizza from Pizzeria Boema, cheese boards from High Lawn Farm, and freshly shucked oysters**. 🍕🧀🦪

Even better, the festival supports the **Lenox Library Association** through an on-site silent auction and raffle, making this celebration of food, wine and community even more special.

🍷 **LENOX WINE FESTIVAL**
📅 Saturday, September 19, 2026
📍 The Barn at Pizzeria Boema – Lenox, MA
🥂 Wine, craft beer & cider tastings
🍴 Local food & more

Turn the festival into a Berkshire weekend with a stay at the **Hilton Garden Inn Lenox/Pittsfield**. Enjoy a beautiful September day in Lenox, raise a glass at the festival, and then return to the comfort of our hotel.

**Great wine, great food and fall in the Berkshires — sounds like a pretty good reason to visit!** 🍷🍁🏨



Learn more at: https://darebottleshop.com/events/lenox-wine-festival/

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/28/2026

🍎🍂 **One of Lenox’s Favorite Fall Traditions Is Back!** 🍂🍎

Fall in the Berkshires is something special, and the **45th Annual Lenox Apple Squeeze** is the perfect reason to plan a getaway! Join the fun on **Saturday, September 26th from 10 AM–5 PM** as historic downtown Lenox transforms into a lively fall festival.

Stroll through the village and explore **more than 100 artisan and food vendors**, enjoy live music throughout downtown, discover unique handmade goods, and treat yourself to plenty of delicious fall flavors. There will also be family activities and a kids’ carnival, making this a great day out for visitors of all ages.

And of course, late September means the beautiful Berkshires are beginning to show off their fall colors — the perfect backdrop for a day spent exploring Lenox. 🍁

Best of all, when you stay at the **Hilton Garden Inn Lenox/Pittsfield**, you’ll be just a short ride from all the festivities. Enjoy the Apple Squeeze, explore the shops and restaurants of Lenox, then return to the comfort of our hotel and make a full weekend of it.

🍎 **LENOX APPLE SQUEEZE**
📅 Saturday, September 26th
⏰ 10 AM–5 PM
📍 Historic Downtown Lenox
🎟️ Free to attend

Fall weekends in the Berkshires are popular, so start planning your getaway now. **We’d love to welcome you!** 🍂🏨

Learn more at: https://cameronvolastro.com/blog/lenox-apple-squeeze-2023-everything-you-need-to-know

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/25/2026

🎸✌️ **Relive the Music & Spirit of Woodstock in the Berkshires!** ✌️🎸

Looking for a great reason to plan a last-minute getaway? **Back to the Garden 1969** returns to **The Colonial Theatre in Pittsfield on Sunday, August 30th at 2 PM** for an incredible celebration of the music that defined a generation!

This full theatrical concert experience brings the sights and sounds of Woodstock back to life with music made famous by **Jimi Hendrix, Janis Joplin, Crosby, Stills, Nash & Young, Santana, Joe Cocker, Jefferson Airplane, Creedence Clearwater Revival, The Band, Sly & The Family Stone**, and many more. 🎶

It’s more than a tribute concert — period costumes, immersive lighting, video, authentic sound bites, and storytelling help recreate the atmosphere and energy of the legendary 1969 festival.

Best of all, **The Colonial Theatre is right here in Pittsfield**, just a short ride from the **Hilton Garden Inn Lenox/Pittsfield**. Make a weekend of it, explore the Berkshires, enjoy an afternoon of legendary music, and then return to relax in comfort with us.

🎸 **EVENT DETAILS**
📅 Sunday, August 30th
⏰ 2:00 PM
📍 The Colonial Theatre – Pittsfield, MA
🎶 Back to the Garden 1969

Dig out the tie-dye, embrace the Woodstock spirit, and turn the show into a Berkshire getaway. **We’d love to welcome you!** 🌄🏨



Learn more at: https://www.berkshiretheatregroup.org/event/back-to-the-garden-1969/

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/24/2026

🎤🤠 ** There are still tickets lets to see Carrie Underwood at Tanglewood this weekend, so plan your visit now!!** 🤠🎤

Country music fans, this is a BIG reason to plan a late-summer getaway to the Berkshires! **Eight-time GRAMMY Award winner Carrie Underwood** will take the stage at **Tanglewood on Saturday, August 29th at 7:00 PM** for her very first performance at the legendary venue.

From powerhouse vocals to the songs that have made her one of country music’s biggest stars, this promises to be an unforgettable night at one of the Berkshires’ most iconic summer destinations.

And when you stay at the **Hilton Garden Inn Lenox/Pittsfield**, Tanglewood is just a short drive away! Spend the afternoon exploring Lenox, grab dinner nearby, enjoy an incredible evening of live music, and then return to the comfort of our hotel instead of making the long drive home.

🎶 **EVENT DETAILS**
📅 Saturday, August 29, 2026
⏰ 7:00 PM
📍 Koussevitzky Music Shed at Tanglewood
🎤 Carrie Underwood – Tanglewood Popular Artist Series

Concert weekends are some of the most exciting times to visit the Berkshires, so don’t wait until the last minute. **Book your stay with us and turn Carrie Underwood at Tanglewood into a full Berkshire weekend getaway!** 🌄🏨🎶



Tix and more info at: https://www.bso.org/events/carrie-underwood-2026?performance=2026-08-29-19:00&source=ecat

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/19/2026

🎢☀️ There's still some Summer left, and adventure awaits at Jiminy Peak’s Mountain Adventure Park! ☀️🎢

When guests stay with us at the Hilton Garden Inn Lenox/Pittsfield, they’re just a short drive from one of the Berkshires’ most exciting summer destinations — the Mountain Adventure Park at Jiminy Peak!

Whether you’re traveling with kids, friends, or looking for a fun date-day activity, the Adventure Park offers something for everyone. Take a thrilling ride on the famous Mountain Coaster, soar through the air on the Soaring Eagle Zip Ride, challenge yourself on the ropes course, or enjoy scenic chairlift rides with incredible mountain views. There are activities for adventurers of all ages, making it easy to spend an entire day creating unforgettable summer memories.

The Mountain Adventure Park is one of our favorite recommendations for guests looking to experience the outdoors, enjoy some excitement, and take in the beauty of the Berkshires all in one place.

After a day of fun, return to the comfort of the Hilton Garden Inn Lenox/Pittsfield and relax in our spacious accommodations while planning tomorrow’s adventure.

🎢 Thrilling attractions
🌄 Beautiful mountain views
👨‍👩‍👧‍👦 Fun for the whole family
🏨 Comfortable accommodations nearby

Sounds like the perfect reason to plan a Berkshire getaway this summer!

Tix and more info at: https://www.jiminypeak.com/.../Mountain-Adventure-Park/

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/17/2026

🎸🌾 **Neil Young Fans — This One’s for You!** 🌾🎸

Looking for another great reason to plan a fall getaway to the Berkshires? **Harvest & Rust: A Neil Young Experience** is returning to **The Stationery Factory in Dalton** on **Saturday, September 26th**!

Known as one of the Northeast’s premier Neil Young tribute bands, Harvest & Rust takes audiences on a journey through more than **70 Neil Young songs**, including music from his legendary solo career as well as his years with Buffalo Springfield and Crosby, Stills, Nash & Young.

This special **unplugged and acoustic performance** offers a more intimate way to experience the songs that have defined generations — and with a constantly changing setlist, no two Harvest & Rust shows are quite the same.

🎶 **EVENT DETAILS**
📅 Saturday, September 26, 2026
🚪 Doors: 7:00 PM
🎸 Show: 8:00–10:00 PM
📍 The Stationery Factory – Dalton, MA
🎟️ All Ages

Turn concert night into a full Berkshire getaway with a stay at the **Hilton Garden Inn Lenox/Pittsfield**. Enjoy a beautiful fall day exploring the Berkshires, head out for an evening of classic music, and then return to the comfort of our hotel to relax.

Tix and more info at: https://www.simpletix.com/e/harvest-rust-a-neil-young-experience-tickets-279435

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

Harvest & Rust returns to the Stationery Factory Saturday September 26! Widely regarded as one of the premier Neil Young tribute bands in the Northeast USA, Harvest & Rust is celebrated for its stirring, deeply authentic performances.

08/14/2026

🎤🤠 **Carrie Underwood Is Coming to Tanglewood!** 🤠🎤

Country music fans, this is a BIG reason to plan a late-summer getaway to the Berkshires! **Eight-time GRAMMY Award winner Carrie Underwood** will take the stage at **Tanglewood on Saturday, August 29th at 7:00 PM** for her very first performance at the legendary venue.

From powerhouse vocals to the songs that have made her one of country music’s biggest stars, this promises to be an unforgettable night at one of the Berkshires’ most iconic summer destinations.

And when you stay at the **Hilton Garden Inn Lenox/Pittsfield**, Tanglewood is just a short drive away! Spend the afternoon exploring Lenox, grab dinner nearby, enjoy an incredible evening of live music, and then return to the comfort of our hotel instead of making the long drive home.

🎶 **EVENT DETAILS**
📅 Saturday, August 29, 2026
⏰ 7:00 PM
📍 Koussevitzky Music Shed at Tanglewood
🎤 Carrie Underwood – Tanglewood Popular Artist Series

Concert weekends are some of the most exciting times to visit the Berkshires, so don’t wait until the last minute. **Book your stay with us and turn Carrie Underwood at Tanglewood into a full Berkshire weekend getaway!** 🌄🏨🎶



Tix and more info at: https://www.bso.org/events/carrie-underwood-2026?performance=2026-08-29-19:00&source=ecat

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/12/2026

🎸🔥 The Sounds of Santana Are Coming to the Berkshires! 🔥🎸

Looking for another great reason to plan a summer getaway with us? Sounds of Santana takes the stage at The Stationery Factory in Dalton on Saturday, August 22nd, bringing the legendary music of Carlos Santana to life!

Led by Minneapolis guitarist Joe Cruz, this electrifying 7-piece band celebrates Santana’s incredible catalog with favorites including Black Magic Woman, Oye Como Va, Smooth, The Game of Love, and more. Get ready for an evening filled with soaring guitar, Latin rhythms, and songs you know and love.

🎶 EVENT DETAILS
📅 Saturday, August 22, 2026
🚪 Doors: 7:00 PM
🎸 Show: 8:00–10:00 PM
📍 The Stationery Factory – Dalton, MA
🎟️ Tickets: $25–$30

Best of all, it’s just a short drive from the Hilton Garden Inn Lenox/Pittsfield. Enjoy the concert, then head back to the comfort of our hotel instead of making the long drive home.

Make a weekend of it and experience live music, great dining, beautiful Berkshire scenery, and everything else our area has to offer. Book your stay with us and turn concert night into a Berkshire getaway! 🎶🏨🌄



Tix and more info at: https://www.simpletix.com/e/sounds-of-santana-tickets-275438

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/11/2026

🎉🍺 Raise a Glass at the Art of Brewing Festival! 🍺🎉

Looking for the perfect summer event during your stay in the Berkshires? Don't miss the 8th Annual Art of Brewing Festival at the Norman Rockwell Museum on Saturday, August 15, 2026!

Spend the afternoon sampling craft beers from regional breweries, enjoying delicious local food, listening to live music, and exploring the beautiful museum grounds. It's a unique event that combines the Berkshires' thriving craft beer scene with one of the region's most iconic cultural destinations, making it a must-visit for beer lovers and art enthusiasts alike. citeturn0search0turn0search4

Located just a short drive from the Hilton Garden Inn Lenox/Pittsfield, the festival is the perfect excuse for a summer getaway. Spend the day tasting local brews, exploring the museum's world-renowned exhibits, and soaking in the beauty of the Berkshires before returning to relax in the comfort of our hotel.

🍺 Regional craft breweries🎶 Live music🎨 A beautiful museum setting☀️ One of the Berkshires' favorite summer traditions🏨 Comfortable accommodations just minutes away

Plan your August getaway today—we can't wait to welcome you!

Learn more at: https://www.nrm.org/events/8th-annual-art-of-brewing-festival/

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com

08/07/2026

There's still a few weeks left to enjoy summer in the Lenox/Pittsfield area of the Berkshires!

Check out this awesome post that has features an excellent Bershires itinerary! Most of the items are just a short ride from us, making us the perfect anchor point!

6 Amazing Things to Do in the Berkshires This Summer ☀️⛰️

🚤 Rent a pontoon on Pontoosuc Lake – Spend the afternoon cruising, swimming, and soaking up the sun on one of Pittsfield’s most accessible lakes.
🎶 Berkshire Busk! – Every Friday and Saturday night all summer in downtown Great Barrington, the streets come alive with music, fire performers, artists, and more. Free, fun, and full of local flavor.
🌄 Drive to the top of Mount Greylock – The highest point in Massachusetts, with breathtaking views that stretch into 5 states. Bonus: You can drive all the way to the summit!
🗿 Explore the sculpture trail at The Mount – Once home to Edith Wharton, this estate in Lenox blends literary history with lush gardens and rotating outdoor sculpture exhibits.
🛶 Paddle the Stockbridge Bowl – Calm, scenic, and surrounded by mountains. Bring a kayak or paddleboard and catch golden hour on the water.
🏛️ Wander through Hancock Shaker Village – A living history museum with iconic round barns, peaceful walking trails, and fascinating insight into a unique way of life.

Thanks to www.instagram.com/visittheberkshires for the awesome suggestions!

Be sure to like this post 👇 and our page 👆🏻 for more amazing content, and follow this link to book with us! >>> http://www.LenoxPittsfield.HGI.com