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Explore the Berkshires For The Holidays

Exploring The Berkshires For The Holidays

In the last segment of our tour, we were going to explore the Berkshires for the holidays. It was very picturesque and felt like something right out of a Norman Rockwell painting. In all actuality, it was a scene for a Norman Rockwell painting, which I got to see in person. 

Checking-In To The Quaintiscential Red Lion Inn

The ride from Historic Deerfield to Stockbridge, Massachusetts is about an hour up into the Berkshires. Our first stop, Stockbridge was where we checked in. It is home to the Red Lion Inn. We received a key to our room, and then a ride up the old-fashioned elevator, which is a requirement as part of the check-in process of this adorable inn. 

I quickly dropped my things in my room and started taking pictures and videos. I wanted to capture all of the details! It was so charming and welcoming and familiar. I can’t do it justice with words so here are some photos. 

Winterlights At Naumkeag

After grabbing the content that I could, I met everyone in the lobby so we could catch the bus to the Winterlights at Naumkeag. You can still purchase tickets now to see these lights up until January 6th. It was a short 5-minute bus ride to the Winterlights. This event has been hailed as one of the best public holiday light displays in the country for 3 consecutive years by USA Today! 

We could have easily spent three hours in this place with the variety of lighting displays! The content creators in us were just going wild! Since we went in the middle of the week, the crowds weren’t an issue for us at all! We took our time and enjoyed playing around in the trees and through the light tunnels! It was so much fun! But we did have dinner reservations to get to so we had to scurry about and grab the last of the shots that we wanted and get back onto the bus to our driver back at the Inn. 

Here’s a sampling of what you can see at the Winterlights at Naumkeag. It was a blast and I want to try to get back to them before they turn off for the season on January 6, 2024. Halfway through the path, there is a concession stand with hot beverages and a fire pit! 

Alta Restaurant & Wine Bar

We arrived back at the Inn and drove about 10 minutes over to Alta for dinner. This restaurant was fantastic! The meal was delicious, the mood was comfortable and happy, festive, and laid back. It was a small location, but it was cozy. Described as “Inspired Mediterranean cuisine mixed with wines from around the globe creates your friendly local dining spot.” This couldn’t be more true. 

We enjoyed our time together talking over drinks and then getting to know each other more over appetizers, and by dessert, we were sharing our love stories and future dreams! It was wonderful, all of it. 

At the end of the meal we met the chef and he talked to us about his dreams becoming a reality with the opening of this restaurant. ALTA RESTAURANT & WINE BAR joined the beautiful Lenox village in the summer of 2008. The humble creation of three passionate restaurateurs, Alta is a favorite of both locals and visitors alike. They pride themselves in always having the freshest organic ingredients. And their wine list is extensive. They also take pride for not only providing delicious food and wine, but exceptional service as well.

It was everything and more! We all enjoyed our time at Alta and I will also recommend this for my future girls’ trip getaway, or a Valentine’s Getaway to the Berkshires must-do list! I have so many ideas about why you need an excuse to explore the Berkshires!

The Night At The Inn

When we arrived back at the Inn Ameera and I wandered through the Tavern where she spotted a kitty running across the hall. Then I remembered the Innkeeper said something about a heated pool outside so we went to explore and found it! And it was clean and it was VERY warm! I forgot to pack my bathing suit. If I did, I definitely would have gone in the pool with Ameera! She told me she was going to get in it the following morning though! And she did!

After we toured each other’s rooms we said goodnight and retreated to our rooms for the night. I opened one of my windows because it was an old hotel and I wanted to feel the cold air and hear the distant train. There was a lit Christmas tree right outside my room and it looked so pretty. I felt like it was a scene in the Polar Express. The air was cold and swirly with snow flurries but the warmth from the hotel room was nice while I sat by the open window. I was just enjoying some quiet time with my thoughts. 

To end my wonderful day, I turned on the Hallmark Channel and set my TV timer to sleep mode and I drifted off to sleep.

Breakfast at the Red Lion Inn

The following morning I was up in time to grab some of the great morning light from the windows in my room, and record some content. There were features in this adorable inn that I wanted to share with my audience. Maybe they’d like to request my room because it had the bear-claw bathtub with a window. I could even imagine a bride getting ready in this suite on the day of her wedding. Or having her bachelorette party here. There are so many options!

After grabbing my video content, I met Beatriz in the restaurant and I ordered some fruit muffins and coffee to have on my way to the Norman Rockwell Museum. It was the perfect breakfast for the type of day we had lined up.

Norman Rockwell Museum

I didn’t know that I was going to enjoy a museum about paintings as much as I did! When you enter the museum during the holidays you will be greeted by a beautiful train and village set. I love model trains and villages! The tour guides explained to us that the village that the train is set up with represents the Red Lion Inn and the Old Main Street it resides on.

Exploring the Berkshires For the Holidays

I feel that the tour guides of the museum really make a difference when you listen to what they have to share. It’s little bits of knowledge like that that you should take a guided tour when visiting museums. They want to share the little secrets and quirks of the artists.

For the holidays the Norman Rockwell holiday prints are on display. Along with other popular pieces. You can find every single cover for the Saturday Evening Post downstairs where you can listen to a presentation about the history of those cover images.

I don’t want to give away all of the little nuggets I found at the museum so you will have to visit for yourself and spend some time walking the grounds as well! The museum sits on the 36-acre campus. You can enjoy art from other members of the Rockwell family scattered around the lawn. The studio, which was originally located on South Street in Stockbridge is also located on the grounds. The studio building was cut in two and moved to the Museum’s grounds in 1986.

Ventfort Hall Mansion And Gilded Age Museum Tour

This may have been my favorite thing for the day. It’s so hard to pick a favorite, but I really enjoyed wandering around the Ventfort Hall property. I got to imagine the people who lived in this “cottage” back in the Gilded Age. Currently, there is an exhibit on display for Hats of the Gilded Age. Ventfort Hall may look familiar to you as it is from the movie Cider House Rules.  

It’s fascinating to see all of the detail that went into the trim in the home and the stairwells. Everything was so detailed and intricate. And the furniture and small daily used items that were still there were so relatable. They had to brush their hair. They used makeup tables to get ready.

I enjoyed touring Ventfort Hall. If you want to give back, you can volunteer your time in and outside the mansion Check out their volunteer opportunities to find what may suit you! I wish I lived closer, I would love to volunteer in their gardens in the warmer months!

Lunch at Haven Cafe & Bakery

With all of our museum touring and mansion walking, I worked up an appetite! Lunch at Haven was going to be the last stop of our day and for the trip. The warm tomato soup and a freshly made toasted goat cheese sandwich with cranberries were so delicious! The owner takes pride that the priority at Haven is food and community.

Their mission is to offer “high-quality food and excellent service to all of our guests – whether you need a fresh cup of great coffee to go, a healthy delicious breakfast to sit down with, a tasty life enhancing meal to take home or if are planning a catered event for dozens of friends and family.”

They also pride themselves in their support of a great big team of local organic farmers, environmentally conscious and epicurious distributors.

I enjoyed the atmosphere. I watched as locals came in and picked up lunches, people recognized one another, and the chef was always around checking on things to make sure everything tasted exactly as it should! This is a great place to stop by and pick up a picnic lunch to take to enjoy at the ground of the Normal Rockwell Museum or visit a local vineyard or brewery in the Berkshires. 

It was the perfect way to end our day and wrap up our wonderful whirlwind adventure!

I hope you enjoyed our tour of Western Massachusettes for the Holidays as much as I enjoyed touring these locations! I know my photographs can’t do justice to what you will see in person. But check out my YouTube channel where I also post video recaps of my adventures!

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