Great Barrington, MA

Appalachian Trail Great Barrington

When we moved up to Maine from North Carolina six years ago, I remember how excited I was that we’d only be a few hours drive from so many New England destinations I’d always wanted to visit. The Berkshires were of course high on that list of places, and thankfully we’ve had a chance to visit this stunning region in western Massachusetts three times in the last couple of years. Until this most recent visit, our trips had always taken us to North County – North Adams & Williamstown, but as part of our trip to Hudson, NY we decided to take the opportunity to familiarize ourselves with the South County region, specifically the charming town of Great Barrington.

Briarcliff Motel

In general, it’d probably be fair to say that the years haven’t been kind to the mid-century Americana classic road-trip motel. Scattered along seemingly every state road, motels represent a time before big box “cookie-cutter” accommodations, where road trips were an integral part of vacationing and where you spent the night had a distinctly local feel. Now days, motels largely get ignored and have started showing their age, as was probably the case with the Briarcliff Motel property before husband and wife, Richard Proctor and Clare Weatherall injected it with a passion for service, a creative eye for design, and the desire to provide an affordable B&B-style accommodation in the middle of the Berskshires. I’d wanted to stay at the Briarcliff Motel since reading about the renovated 1960s motel turned bed & breakfast in this Food & Wine article. Not only is the Briarcliff incredibly dog-friendly, centrally located near a number of hiking trails and with a wall of past four-legged visitors, the rooms are comfortable and stylish, the breakfasts are delicious, and the co-owners and staff are extremely friendly and helpful. We couldn’t have asked for a better place to rest our heads at night during our stay.

Rubiner’s Cheesemongers + Rubi’s

Lunch was the first thing on our minds when we arrived in Great Barrington, so we headed straight to Rubi’s for a couple of sandwiches. Known for the cheese-mongering in the next room, the list of sandwiches, creatively centered around their cheeses, was impressive. After finishing up our delcious lunch, we were eager to browse the selection at Rubiner’s Cheesemongers, right next door. It wasn’t easy to select one of their dozens of fine cheeses, but we ended up settling on the Goat Lady Gouda to share with our friends in Hudson, and we’ve been dreaming of finding it locally ever since.

Prairie Whale

Our brunch at the Prairie Whale, on the outskirt of Main Street in Great Barrington, was another pleasant dining surprise. We sat outside with Orvis and enjoyed a delicious and leisurely brunch of a burger and eggs in the warm sun. I had a second to peek my head inside at the bar, and only wished that we would have time to return for a drink later, which sadly didn’t play out. Next time, for sure – we enjoyed our meals at the Prairie Whale so much that we’re certain there will be a next time!

SoCo Creamery

We had SoCo Creamery ice cream multiple times on our last trip to Williamstown, so when we found out that there was a SoCo location in downtown Great Barrington, there was no question as to where we’d be having an afternoon treat. Just as creamy and delicious as we remembered, SoCo ice cream is a Berkshires must for any ice cream lovers like ourselves.

Benedict Pond + Beartown State Forest

Richard & Clare made the fantastic recommendation to take Orvis for a hike in nearby Beartown State Forest. The loop trail meanders around the Benedict Pond, briefly overlapping the Appalachian trail, and afforded Orvis a couple of different opportunities to take a quick dip, which is always a highlight of any hike for us!

For our next trip: a hike up Monument Mountain and lunch at Bizalion’s, followed by dinner at Allium (the sister restaurant to Williamstown’s Mezze). Fingers crossed we don’t have to wait too long to plan another visit to Great Barrington!

Briarcliff Motel Great Barrington

Briarcliff Motel

Briarcliff Motel Bathroom

Briarcliff Motel Breakfast

Briarcliff Motel Great Barrington

Great Barrington Briarcliff Motel

Pet Friendly Briarcliff Motel

Rubiner's Cheesemongers

Rubiners Great Barrington

Prairie Whale Great Barrington

Prairie Whale

Prairie Whale MA Brunch

Prairie Whale Salty Dog


Prairie Whale Brunch

Prairie Whale Burger

Great Barrington Prairie Whale

Michael and Orvis

Benedict Pond Great Barrington


Beartown State Forest MA

All photos taken by Meredith Perdue for Map & Menu. 

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