WHY WE LOVE IT HERE | A country retreat for city-folk dating back to the early 1800's, call her old-fashioned but there is nothing stodgy about the beautiful Berkshires. Elegant homesteads and gilded-age mansions, gardens-a-plenty, picturesque Americana towns, antique shops and a food trail to rival any farm-to-table culinary destination. Pack your bags and your kids and head to Massachusetts!!
BEST TIME TO GO | To truly enjoy the below itinerary we suggest a summer visit.
WHAT TO PACK | Think preppy - this region of Massachusetts was the epicenter of the Prep movement. Floaty dresses for porch hangs, comfortable shoes for hiking and sandals for around town.
TIPS | You might consider planning a visit around the Tangelwood and Jacob’s Pillow performance schedules. And if you’re into cool old things, consider coordinating your stay with the Brimfield Flea Market.
SLEEP
The Red Lion Inn: for history buffs and vintage lovers, there is no greater place to lay your weary heads than this great American Inn. Full of an impeccable collection of antiques, charmingly creaky floors, an epic porch with rocking chairs to watch the world pass by and a blazing hearth for chilly evenings in the lobby. Rooms start at $265/night.
EAT: BREAKFAST
Break-your-fast: at the Red Lion Inn where the blueberry pancakes reign supreme. Add a side of local Berkshire pork sausage - obviously. Be sure to pay a visit to the house cat and ride the old-timey elevator for a glimpse back in time.
Breakfast at Haven in Lennox is a locals-only must - seasonal, fresh and homemade.
ENERGIZE
Norman Rockwell Museum: a visit to Stockbridge is incomplete without spending some time in these history-filled halls. Norman lived and painted for much of his life in this community and the largest representation of his work can be found lining the walls. Kids will appreciate the paintings of children their own age.
SNACK
The Scoop, Lenox: for heartbreakingly creamy ice cream
Or satiate a sweet tooth craving in Great Barrington with a scoop or two of the inspiring flavours at SoCo Creamery
PLAY
Head to Great Barrington to poke around the sweet shops that line Main Street. One Mercantile for copper mint julep mugs, ceramics & salt water taffy, Rubiner's Cheese Mongers & Grocers for some funky fromage and of course, Tom's Toys.
Tour the guilded age mansion and gardens of Naumkeag. If you happen to visit over a Thursday evening, stay for the live music and food.
EAT: LUNCH
Widow Bingham's Tavern, Stockbridge: this century old Dining room is part of the Red Lion Inn, the pub has been satiating appetites for lunch and dinner since the 1800's. You'll enjoy hearty soups, fresh fare and savoury classics - plus a kids menu for picky minis.
FROLIC
Spend an evening channeling the life and times of Edith Warton at The Mount & Gardens (her beloved country estate). Fridays and Saturdays throughout the summer offer live music and jazz as part of their After Hours program on the terrace (5:00 - 8:00 PM), while Fall is a great time to take a ghost tour of the home and property. Admission for children is free.
CAFFEINATE
Stockbridge Coffee & Tea - their housemade roasts are some of the best in the Berkshires!
Or pop by Fuel in Great Barrington
INSPIRE
Jacob's Pillow is an iconic dance festival and historic landmark nestled in the Berkshires. Performances run from June 17 - August 27. If you are lucky enough to plan your visit during these summer dates, be sure to attend an Inside/Out performance - free and open to the public showcasing a wide range of dance companies and dance styles. Each performance wraps up with an audience q&a. Running Wednesday - Saturday.
If Tanglewood is in season (June - August), be sure to catch a matinee at Seranak Cottage, the summer home of the Boston Symphony Orchestra since the 1930's. You can order a picnic online via their website, or head to Ne Jaime's Wine Cellarsin Stockbridge for the best in gourmet fare - pre-packaged picnics or self-curated. They'll even pack your wine or beer on ice and provide serviettes and silverware!
EAT: DINNER
Frankie's Ristorante Italiano, Lenox: Casual and fun American Italian cuisine - very welcoming to young families.
Make your way to Table Six at the Kemble Inn for an early dinner. Grab a table on the grass and let your kids run amok across the vast lawn - it's enormous & inviting - while the adults enjoy a *moment of peace & tranquility *moment being relative of course.
DATE NIGHT
Prairie Whale, Great Barrington: Former brooklynite and well-known restauranteur, Mark Firth, has brought his farm-to-table cuisine closer to the farms themselves. Serving delicious, seasonal, hyper-local meat and produce, the menu changes daily. Better than Brooklyn!! lands so rich they compared them to butter. Humble, delicious local fare paired with craft cocktails.
