Hilton Garden Inn Lenox Pittsfield

09/09/2026

🎃🍂 Spooky Season Is Coming to the Berkshires from Oct 1 to Oct 31! 🍂🎃

Fall is already one of the best times to visit the Berkshires, but Halloween season gives you even more reasons to plan a getaway! The Trustees are bringing back a lineup of festive Halloween experiences, including two favorites right here in the Berkshires.

🎃 The Incredible Naumkeag Pumpkin Show in Stockbridge transforms the historic property into a glowing autumn wonderland filled with thousands of jack-o'-lanterns, hundreds of mums, pumpkins, and creative displays. Stroll the illuminated grounds and gardens for a magical fall evening the whole family can enjoy.

👻 For something a little spookier, Ghost Tours at The Old Manse in nearby Concord offer an eerie journey into the property's fascinating past, complete with stories of the people who once called it home.

Of course, the Naumkeag Pumpkin Show is especially easy to add to your stay at the Hilton Garden Inn Lenox/Pittsfield. Spend the day leaf peeping, exploring our charming Berkshire towns, and enjoying everything fall has to offer before heading to Naumkeag as the sun goes down. 🍁

Then return to the comfort of our hotel and do it all again the next day!

🎃 Pumpkins + 🍁 fall foliage + 👻 Halloween fun + 🏨 a Berkshire getaway = the perfect October escape!

Learn more at: https://thetrustees.org/program/naumkeag-pumpkin-show/

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

09/07/2026

🇺🇸 Happy Labor Day from the Hilton Garden Inn Lenox/Pittsfield! 🇺🇸

Today, we celebrate the hard work, dedication, and contributions of workers everywhere. We hope you’re enjoying a well-deserved opportunity to relax, recharge, and spend time with the people who matter most.

Here in the Berkshires, Labor Day is also a wonderful time to soak up the final days of summer. From scenic drives and outdoor adventures to incredible dining, arts, culture, and charming downtowns, there are so many ways to enjoy a long weekend in our beautiful corner of Massachusetts. 🌄☀️

Whether you’re visiting us for the holiday weekend or planning a Berkshire getaway later this fall, the entire team at the Hilton Garden Inn Lenox/Pittsfield looks forward to welcoming you.

Wishing everyone a safe, relaxing, and very Happy Labor Day! ❤️🤍💙

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

09/04/2026

🐾✨ Traveling with your furry friend? We’ve got you covered! ✨🐾

At the Hilton Garden Inn Lenox/Pittsfield, we’re proud to be pet friendly — because adventures are always better when your four-legged companion can join you. Whether you’re exploring the Berkshires, visiting family, or just getting away for the weekend, your pet is welcome to stay right by your side.

Enjoy comfortable rooms, nearby walking areas, and the convenience of bringing your whole family along — paws included. 🐶❤️

Pack the treats and we’ll handle the rest. We can’t wait to welcome you and your furry travel buddy!



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

08/31/2026

🍷🍂 **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