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  • Writer's pictureKarin Ashley

Berkshires With Baby

Western Massachusetts is known for beautiful scenery, art, culture, and dining - all things that are really popular with the newborn to toddler genre. Babies love long drives through the changing foliage and stops at scenic overlooks, right?

Wrong, they don't care. But, our late spring trip to the cluster of quaint New England villages has proven that a cute little romantic trip through Berkshire County can (and should) be done with kids.

We (my husband, myself, and an almost-one-year-old babe) had a tight 48 hours in western Massachusetts, a place none of us had ever been. It is a short 2-hour trip by car from Boston, which makes it a totally do-able country weekend trip from the big city. There are a few flight options with shorter drives - Albany, NY (ALB, 1ish hour by car) and Hartford, CT (BDL, 1 hour by car). Albany was the cheapest option for our travels from the midwest, and I found the airport to be sufficiently baby-friendly.

After a quick and painless rental care pick-up with car seat installation (praise be) we embarked on the last 1 hour leg of our travel day, a beautiful drive with a YoYo Ma soundtrack, the only music that puts our lil guy to sleep. I will take that over Baby Einstein Playdate Fun which has a permanent place in my brain even 11 years after my first baby required it for docility in the car.

Life House Berkshires, a roadside motel turned boutique writer's retreat, was the perfect landing place after a long day of travel. What I loved about staying at Life House with a baby:

  1. I didn't have to bring a pack-n-play. The staff quickly and joyfully delivered and set up a Guava Portable Crib while we walked around, admiring the property. We have a guava crib and love traveling with it, but it was nice to have one less thing to bring! Setting it up and providing sheets for us was an extra little detail that made us feel cared for.

  2. Outdoor space to exercise little legs. While the staff was setting up our crib and we had a few minutes before needing to grab dinner, we got drinks at the Life House Cocktail Bar & Restaurant. The little one crawled around while we decompressed with a glass of wine and a manhattan.

  3. Breakfast was simple and delicious - overnight oats, eggs and toast, yogurt with granola, coffee. Our favorite was the overnight oats with chia and berries. The restaurant staff helped us plan our day with restaurant and excursion recommendations, and they didn't disappoint!

  4. The mini-bar was the absolute best mini bar I have ever seen. Healthy snacks, good booze, Hu chocolate bars...need I say more?

  5. It's beautiful. The clubhouse, the rooms, the view, the food. It felt like we were at an expensive resort, but was still cozy and approachable enough to enjoy as a family.

In no particular order, here are the places we visited on our short-but-sweet trip:

Olivia's Overlook, West Stockbridge

This is a great place to get out and stretch your legs, and admire the view of the Stockbridge Bowl lake. There are a few trailheads here if you are the hiking type!

Hilltop Orchards

Two words: cider donuts. Also: Cider tastings. Grab a tasting flight and a few donuts, and head over to a picnic bench in the middle of an apple orchard. You can walk around the orchard, which has access to a trail system, and let the babies run/crawl wild. The owners were so incredibly friendly, and knowledgable about the area. They had a lot of other goodies available in their cute little farm store.

High Lawn Dairy

I wish we had all of our kids with us for this stop, as it was one of my favorites, and the most kid-friendly! It's the cleanest/least-smelly dairy I've ever been to. The farm store was beyond cute, and I grabbed several local-made goodies. We got a cheese and cracker box, some probiotic sodas (we are old) and ice cream. There were so many options! Picnic benches were available outside the store, many of which were handicap accessible! In fact, I found the entire place to be pretty accessible. They had new calves in the barn, which was a highlight for the baby (and us, if we're being honest).

The Mount - The Edith Wharton Estate

Another place I wish my bigger kids could have experienced! This place looks like only grandmas would visit, but I think all ages of children would enjoy it. We went before the interior was open to the public (summer hours only), but the grounds are open sunrise to sunset year round. There are lots of little trails to explore, flowers to admire, other people's puppies to pet. I wish we could have seen the cafe and bookstore. I guess a return trip is in order!

Downtown Lenox

Our favorite shops were The Bookshop and accompanying Get Lit wine bar (with a name like that, we had to check it out!) and Dare Bottleshop and Provisions. We walked around and window-shopped a bit, and poked our heads in a few delicious-smelling bakeries.

Patisserie Lenox was on our list to return to, but we never did try one of the many gorgeous pastries. If you go, please have a croissant for me!

Haven Cafe

I wish we would have been here for breakfast, but the lunch was great! I love that they had local organic greens, and there were plenty of bebe-friendly items on the menu. I had a sandwich and a latte while the staff gave endless compliments on the cuteness of my baby (I wholeheartedly agree).


A hotel restaurant (it's in a Hilton Garden Inn) that doesn't suck! I would call this Asian Fusion, as the menu had Japanese, Chinese, and Korean options. I had a Bibimbap bowl with bulgogi, and was able to portion off enough ingredients to feed the baby without ordering off the kids' menu (hard pass on the $10 grilled cheese). The staff was sweet, and the hotel looked like a nice option for lodging!


Our favorite stop! I made reservations in advance because I wanted to make sure we didn't miss out. We considered this our 12 year anniversary dinner, which of course was crashed by the babe. Their outdoor patio was perfect for an early May evening, and being an extrovert, I made friends will all of our fellow diners (introverts I'm sure are cringing). My husband asked the bartender for a selection of drink garnishes to feed/entertain the baby with. I figured my husband would come back with a lemon slice or something, but the bartender curated a little plate of goodies for the baby and brought it out himself - a sweet little touch. Food was amazing, wine selection diverse, and dessert worthy of being eaten by the fist-full.

Overall, a locale known for grown-up activities really proved to be quite accommodating and even fun with a baby. Don't let the fear of traveling with a baby stop you from a quick getaway in the Berkshires!

Bon Voyage!



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