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72 Hours in The Berkshires

A little over a week ago, husband and I were blessed to get to visit friends in the Berkshires, in western Massachusetts. It doesn't get much more Norman-Rockwellian-idyllic than this.

Red Lion Inn

The Red Lion Inn in Stockbridge, MA

To Get There:

Train: Amtrak offers service to Hudson, NY, a quick drive across the boarder from the Berks. You'll need a car once you arrive (closest rental is Enterprise).

Fly: Albany is a small and easily navigable airport a little more than an hour from the Berks. Fly in and rent a car.


Albany Airport

Amtrak train arriving in Hudson, NY Window in the Albany International Airport

To Do:

Eat lunch at Bruno's; delicious sandwiches, including an interesting take on Banh Mi (227 Warren Street, Hudson, NY). The interior is a little rustic and tidy, and they sell a few staples like peanut butter and Sriracha sauce.

Bruno's, Hudson NY

General store items at Bruno's

Grab coffees in downtown Hudson at Moto Cafe (357 Warrent Street, Hudson, NY):

Due Cappuccini

Due cappuccini, per favore.

Check out the beautiful old store fronts all along Warren Street, and pop into a few:

Store Fronts, Warren Street
Cheese Shop, Warrent Street
Warren Street, Hudson, NY

Storefronts and wares to sell

Get in the car and head across the NY-MA boarder to Great Barrington, this is where you'll stay.

The Cottage

Homestead Goals

From whence we hailed during our stay

You won't want to leave.

Side Porch Haven
Kitchen Goals
Wood Burning Stove

Even to make a run to Rubiner's Cheesemongers (264 Main Street, Great Barrington, MA) to get some amazing cheese for gourmet grilled cheese sandwiches. But you will, because it's gourmet cheese, and by now you're hungry.

Rubiner's Cheesemongers

Rubiner's cheese... and local quince and chestnuts

Duck into the Gypsy Joynt (293 Main Street, Great Barrington) to toast to everyone's health before heading home to make supper. Turn in for the night.

Burn off your cheese calories with a morning jog on scenic country roads:

Split Rail Fence

Horseshoe Rail Fence
Massachusetts Barn Garage

Scenic route in Great Barrington, MA

Take some time to relax and be inspired by nature, however you do it best:



Writing poetry and watercoloring

Hop in the car and take a quick drive to the Mary Flynn trail to take in old growth forest along the Housatonic River, cool off in the Ice Glen, and climb up Lauras Tower for a grand view of the Berkshires:

Leo the lion-hearted

Hiking is always better with a dog, if you can bring one with you.

Crossing the Housatonic, taking a quick dip

Cool off in the Ice Glen.

Mossy Ferns in the Ice Glen

Oldest Pine in MA, Mother Tree

Old growth forest in the Ice Glen

Ice Glen Dedication

Climb the fire tower for the amazing views:

Steep Stairs

The Berkshires

Mind your step...

Gorgeous Birch

While you're in Stockbridge to hike the Mary Flynn Trail, stop by the Red Lion Inn and have a glass of wine or a cocktail on the front porch or in the Lion's Den, or just walk through the historic lobby and admire the interior of the inspiration for Norman Rockwell's painting "Stockbridge Main Street at Christmas."

The Red Lion

Lion's Den

Rocking Horse

Red Lion Inn, Lion's Den

Head home, but not before tasting a pint of solar-brewed beer at the Barrington Brewery (420 Stockbridge Rd #7, Great Barrington, MA).

Barrington Brewery

Solar-Brewed Brewery

And on to the meal... in our case, we supped on the best tagine outside of Morocco. (Thank you, @elizabethannorourke and @vikingamerican. You know how to feed us.)



Have a slow and quiet morning before heading to Housatonic for brunch at Pleasant and Main Cafe and General Store (1063 Main St, Housatonic, MA).

Fall Decor
Ceiling Canoe

Pleasant & Main Cafe

Take a snapshot of the iconic water tower in downtown Housatonic to bookend your trip:

Housatonic Water Tower

*I shamefully forgot to mention the stomach and soul-filling dinner we devoured at Prairie Whale on our last night in Great Barrington, with seasonally sourced ingredients. Don't miss it. I believe I forgot because I didn't have any photos from the meal, as I was too busy ravenously devouring my portion of buttermilk fried chicken with honey butter to take any. Whoops.

Happy Travels!

#travel #responsibletravel #TheBerkshires #Massachusetts #relaxation #retreat #brunch #supper #explore #exploremore #NewEngland #adventure

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