I may be a little biased because I grew up nearby, but there’s a slice of Western Massachusetts called the Berkshires, or “the Shire” as the locals would say, that is absolutely glorious. Known for epic fall foliage, excellent hiking and outdoor activities, farm-to-table dining, and classic New England style charm, the Berkshires have people coming from far and wide to enjoy all that it has to offer. Just be warned, this post is full of awesome recommendations including the best place to stay, what to do, and where to eat while visiting the Berkshires, so don’t blame me if you find yourself booking a getaway by the end of this! Keep reading to find out how to have a perfect weekend in the Berkshires, no matter the season. 

Where Should I Stay in the Berkshires?

The Inn at Stockbridge

In order to have a perfect stay in the Berkshires, you need to stay at the perfect bed and breakfast. New England is known for quaint, colonial-style B&Bs, so of course, I found the coziest, cutest, most adorable one in the area: The Inn at Stockbridge. From the decor to the hospitality, to the breakfast and all the little-included amenities, this historic yet modern Inn is exactly what I was looking for in a getaway to one of my most favorite parts of Massachusetts.

The Inn:

For one, the Inn’s history dates back to the early 1900s. The architecture and overall feel speaks to that era, but the current Innkeepers Jeff & Lisa have given it quite a facelift over the past several years. (In fact, they are still renovating to make the Inn the best it can be!)

The property sits on 12 acres of land just outside of the town center, so you get both the proximity of restaurants and shops but also the benefit of a secluded and private property. There is a very warm and inviting ambiance as soon as you walk into the Main House, with crackling fireplaces, French bistro music playing in the background, and a perfect mix of country and modern details.

The Barn & The Shakespeare Room

The property is broken into 3 separate spaces: the Cottage House, the Barn Suites, and the Main House Rooms. I stayed in the Shakespeare Suite located in the Barn and really, really enjoyed my experience.

I loved how the Barn was its own separate entity, and that made it feel extra special to me; it was almost like a retreat within the property with its own little path and everything! The suites located in the Barn are all named after local highlights like the Shakespeare & Company Berkshire Theater Group or the Rockwell Room named after famous local artist, Norman Rockwell. 

My favorite part about staying in the Shakespeare Room was the cozy fireplace and sitting area that make the room feel so relaxing and luxurious. Each night I crawled into one of the fluffy house robes, with a stack of homemade cookies and a cup of tea from the dining area, and sat by the fireplace. I can’t describe how relaxed and happy I was feeling!

The bed was the most comfortable bed I can remember sleeping in, with absolutely divine sheets (which are actually available for purchase). This room was perfect for the getaway I was looking for, with plenty of privacy and added amenities like a private balcony and whirlpool tub in addition. I also loved the little details, like the novels and Shakespearean antiques displayed above the fireplace.

Overall, it served as the perfect escape from daily life and the ultimate space for relaxation!

Wine & Cheese Reception

Another part of my stay at The Inn at Stockbridge that I really loved was the nightly wine and cheese reception. From 4-6pm there are carafes of red and white wine as well as a spread of local cheeses, dried fruits and other goodies to enjoy. This little tradition reminded me of a B&B in Mexico City that I absolutely adored, as well.

The best part of this activity is that you get to meet the other guest staying at the Inn which leads to making new friends all the while enjoying a glass of wine and some local cheese! It’s such a warm and inviting nightly activity to bring everyone together, which I think added so much to my experience.

The Breakfast

One of the (many) reasons I like to stay at family-owned B&Bs is that the breakfast is almost always homemade and especially delicious. This continued to prove true at the Inn at Stockbridge.

With offerings like gingerbread pancakes topped with poached pears and cinnamon whipped cream and baked thick cut applewood bacon, to asparagus swiss and goat cheese quiche with mushroom shallot and tarragon served with lightly dressed greens and a sausage patty, it’s easy to see why I never wanted to leave! In addition, there were homemade scones every morning from oatmeal maple, feta spinach and chive, cranberry ginger and lavender honey. 

There was also homemade granola, local yogurt, and a beautiful fresh fruit cup served with each meal if the entree and scones weren’t enough already. If for some reason you don’t like anything on the daily menu, there are always eggs to order however you like.

In addition, I really enjoyed the homemade cookies, granola bars, fresh coffee and tea which was available just about any hour of the day. There’s even a butler’s pantry where you can find soda, seltzers, hot water, wine glasses, plates or any other thing you could possibly need, all complimentary for guest use.

The Staff

And last but certainly not least, the main reason I usually love staying at family-owned B&Bs and Inns is the staff! Owners Jeff and Lisa were such warm and inviting hosts and their passion for what they do is absolutely contagious. Lisa is a wizard in the kitchen and cooks EVERYTHING from scratch with love.

Jeff is an interior design master and is always looking for ways to improve the look and feel of the already beautiful Inn. Although he has lived in the States for a while and has traveled around the world, I loved how he added little touches of his home country of India, from little decor details to the coffee beans used for morning coffee.

He also mentioned potentially offering the Inn as a space for weddings or other events, so I look forward to seeing all of the beautiful events to happen at this property in the future! 

If you want to experience the true charm of the Berkshires, I absolutely recommend a stay at The Inn at Stockbridge for a weekend getaway you are sure to remember! (And if you want to bring home a memento, they have these cute mugs for sale!)

What should I do in the Berkshires?

Hike to Ice Glen & Laura’s Tower

One of the best things to do while in the Berkshires is to get outside and enjoy the natural beauty of the area. My favorite thing to do is to go hiking, and with over 400 different trails to hike there’s no shortage of ways to experience the great outdoors!

Of these 400 trails, I have a few favorites that aren’t very strenuous, only take about an hour and a half to hike, and have paths starting right outside of Stockbridge (making them really easy to access). In order to find the hikes I’m going to tell you about, I would highly recommend downloading an app called AllTrails.

This is an app with the largest collection of detailed, hand-curated trail maps across the country and will even show you GPS directions once you are on the path. With the app downloaded, head to the explore tab and type in “Stockbridge.” You can type in any location you want, but the two hikes that I recommend come up under the Stockbridge search. Click on either the “Laura’s Tower” or “Ice Glen” option and it will give you all sorts of information about the trail, as well as where you need to go in order to start the hike.

The hike starts out at a beautiful footbridge over the Housatonic River, and then across a set of railroad tracks. Follow your map along the path until you reach a fork that will prompt you to either head towards Laura’s Tower or Ice Glen. Laura’s tower is a lookout tower that gives you a great view of the valley, and Ice Glen is a really fun hike that requires you to climb over boulders and get a little adventurous. This hike is actually my favorite hike from my childhood! Neither of them are too long, so if you have time, I would suggest doing both!

Visit a maple sugar farm

Let’s get one thing straight; you don’t have to go all the way to Canada to get amazing maple syrup! Western Massachusetts is also known for maple syrup production and actually produces 60,000 gallons annually. Maple syrup production not only employs 1,000 local farmers but also allows the preservation of over 15,000 acres for production. Lucky for us, we can actually visit these maple syrup farms (also known as sugar shacks) to get a first-hand look at how this liquid gold is created. The best part about visiting a sugar shack though is the pancake breakfast that is served! The only downside to this activity is that most sugar shacks are only open during maple syrup production season which is from February to April. Ioka Valley Farm is located about a 30-minute drive north of Stockbridge and offers tours, tastings, and breakfast on the weekends. If you’re willing to drive a little bit farther (1 hour from Stockbridge), there’s also the Red Bucket Sugar Shack in Worthington which is famously known among Western Mass residents.

Cross-country ski through the backwoods of the Berkshires

If you happen to be visiting during the winter (which I recommend because it’s a lot less crowded and accommodation costs are much lower) spend an afternoon zipping through the snow on cross-country skis! This might not be an activity for everyone, but I grew up cross-country skiing and to me, it’s the best outdoor activity during the winter months in New England. You can rent skis at Arcadian Shop in Lenox for only $30 per day. There are multiple places that offer day passes in the area including Maple Corner Farm (45 min from Stockbridge) which is where I grew up skiing with my family on the weekends. They have a little lodge with a fire and a small cafe with chili and sandwiches, and even serve a pancake breakfast on the weekends from February to April using their own maple syrup! A day pass here costs $12-$14 depending on the time of day. There’s also Canterbury Farm (25 min from Stockbridge) which also offers ice skating and costs $16 for a day pass, as well as Cranwell Spa & Golf Resort (10 min from Stockbridge) which offers a full day pass for $16 also. Additionally, there are plenty of trails to take at the Inn at Stockbridge which is completely complimentary for guests. 

Experience the history of the Red Lion Inn

The Red Lion Inn is one of the oldest Inns in the United States, and has been in operation for over two centuries! If the colonial facade doesn’t give away its age, the ridiculously low ceilings will. (If you’re 6 feet or taller, be prepared to duck). If you’re feeling fancy, reserve a table at their highly rated main dining room, but if fish and chips with a pint sound more your speed, head over to their tavern.

Looking for something even more casual? Located in the basement level of the Red Lion Inn, the Lion’s Den is an awesome hangout for both locals and visitors looking to grab a pint or a hot buttered rum and enjoy the sounds of local musicians.

Peruse the cute shops in Stockbridge’s town center

WARNING: This activity often leaves you with a very empty wallet. The charming gift shops and boutiques sprinkled around the town center of Stockbridge are almost impossible to resists. Have you ever seen the Gilmore Girls? (Of course you have.) Well, Stockbridge essentially is Stars Hollow. It’s as if this ridiculously charming colonial town has been frozen in 1734!

My favorite shop is called SideTracks, a little boutique in Stockbridge’s town center that sells some of the most unique gifts I’ve come across. The best part is the travel gift corner and the inspiration card section!

There’s also a ton of great shopping in Lenox and Great Barrington if you’re in the shop until you drop mood!

Treat your ears to some live jazz at Castle Street Cafe

I love jazz. I like to find a jazz bar almost everywhere I go. In fact, I even once found a jazz bar in Chiang Mai, Thailand and it was incredible. So, it’s no surprise I found a cozy jazz bar to visit during my time in the Berkshires.

Something to note, Castle Stree Cafe is currently undergoing a facelift and will not reopen until late April 2018. Apparently, there will be a new name, new menu, and a whole new look, but will still have the same great jazz! They typically have live jazz on Friday nights at 8pm.

Where should I eat in the Berkshires?

One of the best things to do while in the Berkshires, is to enjoy a meal at one of the many incredible local restaurants. The Berkshires are known for fresh farm-to-table style dining and definitely take pride in using local ingredients in their cuisine. Below find my top recommendations that will leave your belly feeling very happy.

Once Upon a Table

Tucked down a shop-lined alley off of Main Street in Stockbridge you will find Once Upon a Table, an 11 table bistro serving up hand-crafted cuisine. I went with the vegetable ravioli with an artichoke-lemon butter sauce, roasted red pepper, and parmesan and loved it. Be sure to make a reservation in advance; this place books up fast on the weekends!

Prairie Whale

Named after a term used for pigs back in the 1900s (once it was discovered that you could use pig fat for whale oil in lamps) Prairie Whale is an interesting and inventive restaurant to add to your list! The restaurant is located off of Main Street in Great Barrington inside a converted cottage with beautiful barn wood floors and a cozy-rustic vibe. The menu is chock-full of local and sustainable ingredients including some meats which come straight from the owner’s own farm!

Haven

If you have any room left after a beautiful breakfast at the Inn at Stockbridge, make your way to Haven Cafe & Bakery in Lenox’s town center for some delicious baked goods and excellent coffee. For brunch try the croissant french toast with a cinnamon vanilla latte, and for lunch, the kale or the beet salad. If you happen to have some work to get done, this is a great cafe to post up in for a little while and get a feel for the local scene!

Nudel

For an incredibly unique dining experience, head to Nudel to sample their ever-changing menu (it literally changes nightly). They take the meaning of seasonally inspired food to the next level, and base their menu off of whatever’s in season or whichever ingredients local farmers bring to them that day! They are a team of super passionate chefs and it certainly shows in their beautiful dishes. Nudel is located in Lenox’s town center and is run by local chef, Bjorn Somlo, who has been nominated for dozens of awards.

How can I get to the Berkshires?

From Boston

If you’re visiting Boston for a little while, and want to see a little more of what Massachusetts has to offer,  heading west for a visit to the Berkshires is the perfect weekend getaway! It’s a little over a two-hour drive from Boston but is basically a straight shot west on the Mass Pike.

By car:

You can rent a car from Logan Airport for about $40 a day. This would certainly be the best option, as you’d want to have the freedom to roam once you’re in the Berkshires.

By bus:

If you’re not able to rent a car but still want to get out to the Berkshires, have no fear, it’s possible. You can book a bus ticket from South Station to Stockbridge or Lenox using Peter Pan Bus Lines. The roundtrip ticket will cost you about $85. To get around once you’re in the Berkshires, check out the BRTA website for a schedule.

Have you spent a weekend in the Berkshires? What else would you add to my list?

Wander On,

Wanderluluu xx