Great Barrington, Massachusetts

Fresh air. Fresh food.

Smithsonian Magazine recently named Great Barrington, MA one of the 20 best small towns in America. Memorial Day weekend is a great time to visit Great Barrington, enjoy the outdoor activities of the surrounding Berkshires, and find out if Smithsonian Magazine really knows what it’s talking about.

In addition to fulfilling the needs of anyone seeking fun in the sun, this particular weekend in Great Barrington is also for foodies. Locally grown, farm fresh food is a BIG deal in the Berkshires. This Memorial Day weekend brings Farmed + Foraged: A Weekend of Spring Flavors to the region. Organized by Berkshire Grown, over two dozen area restaurants will participate in what is billed as “a culinary celebration of farmed and foraged seasonal foods.”

Now before you start making calls and packing your bags, this weekend probably isn’t for a family with little kids. We’re proposing an active, bordering on adventurous, 36 hour itinerary. If you have kids that are around seven years or older, a weekend exploring the Berkshires is one small stepping stone towards having children that grow up and want to spend a summer hiking the Alps. And if you’re child free, there’s some fine dining and waterfall hikes in our suggested itinerary that might make more sense for you.

Setting Forth

The best way to deal with the Friday evening crawl on the Mass Pike is to skip it

From downtown Boston, Great Barrington is about a two and a half hour drive without traffic. Therefore, we suggest not starting out until Saturday morning, at which point you should be in full road tip mode. That means hit your nearby Dunkin’ Donuts for some coffee on the way out of town, roll down the windows (and drop the top if you’re so lucky), cue up Exile on Main Street, and put on your perma-grin. Before you know it, you’ll reach Great Barrington ready to fuel yourself up with some lunch before taking on an afternoon hike.

Because it’s in the heart of Great Barrington, which means it has the added benefit of helping you get quickly oriented to town, we suggest you make your first stop lunch at Baba Louie’s at 286 Main Street. It doesn’t hurt that Baba Louie’s features wood fired, all natural sourdough pizzas. Our favorite, “The Dirty Brutto” is topped with, among lots of other goodness, roasted red peppers and pesto.

After lunch, walk or drive down the road to Guido’s Fresh Marketplace at 760 South Main Street. Starting on Saturday at Noon, Guido’s takes part in a Farmed & Foraged Weekend with tastings from local farms and bakeries. This is the spot for tossing some edible treats in your backpack.

Hike Monument Mountain

Sleeping and Eating(because you’ve earned it)

By the time evening rolls around, you’ll need some time to recharge. Looking to pitch a tent? Prospect Lake Park is a typical summer camp spot geared to families. Backpackers can try Mount Washington State Forest, where there is no charge for campsites and they are available on a first-come, first-served basis.

For something with a room and a parking spot right outside your hotel room door, Monument Mountain Hotel may not look like much, but it’s an improvement over chains like Travelodge and Days Inn that can also be found in the area. As a weekend motor lodge, it has some added appeal by providing an outdoor picnic area and horseshoe pits.

If you want a step up in luxury and charm or are interested in a place where every rooms seems to come complete with its own “let’s make it romantic” kit, The Thornewood Inn is the place to call and book.

As we mentioned, it’s a weekend for foodies and we know that you’ll work up an appetite over the course of the afternoon. If you want a casual dining experience, The Well (312 Main Street) is a nice option for a burger and a brew. You can also make dreams come true by placing an order for “Wellness Nachos”, because clearly, the name implies that these nachos are the ones that are good for you. In other words, they’re the nachos you’ve been in search of your entire life. Might as well get two orders.

For more of an upscale culinary experience, the modern European fare at Cafe Adam (325 Stockbridge Road) may be for you. As with The Well, Cafe Adam is a participant in the Farmed and Foraged weekend. If you’re uncertain what exactly modern European fare is, it’s things like goat cheese stuffed dates wrapped in bacon. A dish with goat cheese and bacon in it…admit it, you know you’re going to order that.

Zip Through The Morning 

One last thing

There’s no reason to rush straight home

We’ve covered hiking and zip-lining so far this weekend. Let’s dial down the adrenaline a bit with some sort of leisurely ride before darting back to Boston. Don’t worry, you’ll make it home in time for your Sunday evening lineup.

If you happen to have a kayak or canoe, take it for a ride out on the mountain lakes at Goose Pond Reservation. For something completely different, horseback riding provides an excellent way of exploring the Berkshires. Berkshire Horseback in nearby Lenox offers full day, half day, or one hour ride plans.

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