A Whirlwind Tour Through Stockbridge Massachusetts in New England

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Where’s a great place to escape from Boston or New York urban life for a long weekend? Drumroll please…

Why, Stockbridge, Massachusetts, of course!  Jump in a rental car (or bus), and head North just shy of 3 hours.  You’ll be transported to a town where time stands still, and, for the first time in months, you’ll have a chance to stand still, too.

Day # 1

Step Into Norman Rockwell’s World 12pm

After arriving in Stockbridge, head over to the Norman Rockwell Museum.  Don’t worry about directions, everyone in town will be able to tell you how to get there…and may even have directions printed off!  (Not kidding, this actually happened 3 times!)

Famous for his covers on The Saturday Evening Post, Rockwell called Stockbridge his home for many years.  You may even recognize his famous painting of Main Street, quite popular on the front of Christmas cards.  The white building on the right is the hotel we stayed at.  (Bit of trivia for ya: It’s dark in the painting because back when Rockwell painted it, the hotel was only open seasonly due to lack of heat.  Nowadays, it’s open year round.)

 Pack A Picnic 1:30 pm

Heading “back into town”, (and by this, I mean about 2 quick turns totaling about a 2 minute drive), stop by the Elm Street Market and have them put together some of their sandwich creations for you.  Grab some chips, bottles of water (or wine, depending on how adventurous you’re feeling), and head out to the trails.


Afternoon Hike 2pm

Recommended to me by a local bartender, Laura’s Tower Trail is not to be missed.  Averaging 1.5 miles in length, the trail is marked “moderately difficult”.  The panoramic view at the metal tower located at the summit is worth it though.  Take a break, eat your sammy, have a plastic cup of vino, and take it all in.

Get Settled 4pm

After your hike, head over to the Red Lion Inn, Stockbridge’s historic hotel that has been standing since 1773.  Wow.  Still ever bit as charming as it must have been in its hay day, I was in complete adoration of the antique details the hotel boasts.  From the vintage gated elevator, to the live piano player, to the wood burning fireplace, it was truly like stepping back in time.



The hotel has rooms located in its original building, as well as additional guest houses.  We stayed in the Maple Glen House, a newer addition, and as you can see the room was absolutely perfect.



I particularly loved all the sitting areas the hotel had to offer.  Ideal little nooks to grab your book and wile away the rest of the afternoon, appreciating the flourish of blooms scattered about.



Don’t forget (as I did!) to pack your swimming suit, as there’s both a heated pool and hot tub on site.  I would say don’t forget your workout clothes for the fitness room, but you’re on a R&R getaway, remember?!  Take after me and play with the resident cat instead.


A Little Night Music 9pm

Head downstairs to the Lion’s Den, where they’ll have live music playing for your listening pleasure (as well as trivia nights, open talent nights, or TV dinner nights!), along with bar food favorites.


Day # 2

Country-ish Breakfast 9am

Ahh, is your 24 hours really over so soon?  Before heading out of town, stop by the Main Street Cafe (located next to the hotel) for some breakfast.  Don’t forget the coffee.


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