When hot, crowded, dirty, stressful day-to-day life in New York or Boston has caused city-dwellers’ eyes to glaze over, a weekend in the Berkshire Mountains may be necessary to rejuvenate and put things in perspective. The landscapes that inspired Herman Melville, Nathaniel Hawthorne, and Edith Wharton are sure to have a positive effect on even the most cynical traveler, and there are plenty of man-made musical, culinary, theatrical, and visual creations to further nourish depleted, overworked souls. To get the most out of a full day in the Berkshires, take the following winding path around south county (easiest with a rental car).
Wake up in the historic Red Lion Inn in Stockbridge. This two-century-old New England gem predates the Revolutionary War, and its crest—the red lion—indicated loyalty to the British Crown. However, the lion once had a green tail, subtly indicating sympathy with the cause of Independence. The Inn’s past is connected to Ethan Allen’s Green Mountain Boys, as well as Shay’s Rebellion. After lounging a bit in your individually decorated guestroom, go downstairs to enjoy a lavish breakfast of seasonal berries, Old Chatham Sheep’s Milk Yogurt, house smoked bacon, and Berkshire Apple Pancakes with Ioka Maple Syrup. In the mood for eggs? Then go for the Bulich Farm Shiitake Mushroom Hash & Poached Eggs or the “Lion’s” Frittata with diced prime rib. When the morning’s feast is placed on the table, be sure to break out the phone to capture yourself eating like a king on antique china. Tag #hipmunk or tweet @thehipmunk to make us jealous.
Arrive at the Norman Rockwell Museum as it opens at 10am to see some of this artist’s well-known portrayals of American life in the 20th century. Try to spot his illustrations of the “Four Freedoms” mentioned in FDR’s address to Congress in 1943. For bonus points, stage a living recreation of one of Norman Rockwell’s paintings of smalltown America, using downtown Stockbridge as your backdrop. Show us your best attempt by tagging #hipmunk.
Head one town over to drink a cup of house-roasted coffee in an old train station depot in West Stockbridge. If you find this coffee-lovers’ secret clubhouse, prove it by showing us a cup of the roast of your choice. (Make sure to tweet us which one you picked!) When the buzz has set in, cross the bridge over Shaker Dam and browse through photographs from around the world (many of which were featured in issues of National Geographic) at the John Stanmeyer Gallery.
Drive up to Lenox for the rest of the day. After grabbing a pear croque monsieur or arugula and farro salad at Haven, venture out on foot to explore shops in the quaint historic downtown. See if you can find School House Hill, where Edith Wharton’s character Ethan Frome had his dangerous sledding adventure. Be more careful than Ethan, but get a picture of yourself in sledding position on the hill, and post it on Instagram.
Buy tickets ahead for an evening concert at Tanglewood, summer home of the Boston Symphony Orchestra. The best place to enjoy the music is out on the expansive lawn, so take the rest of the afternoon to procure picnic dinner supplies from Guido’s Fresh Marketplace. With a basket full of good bread, some hummus, dried sausage, cheeses, and a variety of fruits and vegetables, the concert is sure to be a success.
On your drive back to the center of town, be sure to stop off at Chocolate Springs for a sweet interlude. This unique sanctuary (especially on a hot day, when the air conditioning feels heavenly) has a Japanese ambiance, and a variety of handmade bonbons made on the premises. Each one is an edible work of art. Get a ceramic Japanese plate with a few chocolates from the case, such as the gold-dusted “Celebration” bonbon with dark chocolate champagne ganache, the “creme brulee” bonbon striped with white chocolate, the green tea bonbon imprinted with an image of a bonsai, or the erotically shaped “Venus” bonbon with milk chocolate rum ganache. Instagram a pic of your favorite bonbon and, you know, feel free to send us a box!
After this pick-me-up, take your picnic basket, a blanket, and a bottle of wine from Nejaime’s Wine Cellar to Tanglewood. Arrive a few hours early to get the best real estate for both your car and your blanket. Navigate the parking and follow the crowds through one of the gates to find the perfect patch of grass on the lawn, then settle in. Play frisbee or cards, enjoy the wine and food, and relax into the knowledge there is nowhere else you need to be. Before the music starts, make friends with some of your neighbors for the evening. Get a picture sharing a toast with your new pals. Then lie on your back and appreciate the live soundtrack for sunset, twilight, and slowly wheeling constellations.
When it comes to meal time, the restaurants along South Congress and South Lamar can get pretty congested with people. But just a bit East of Congress is 
