GET TO KNOW THE AREA
Hillsdale is smack in the middle of The Hudson Valley and The Berkshires. Below is a selection of things to do and places to eat close to Hillsdale. For our full list of local recs spanning the valley, check out Robert’s ‘Harlem Valley Microtourism’ google maps list here.
ACtivities
BASH BISH FALLS
Short, easy hike along a path with a waterfall at the end.
COPAKE-HILLSDALE FARMERS MARKET
Terrific market filled with local farmers, bakers, and makers. Open Saturday from 9-1. Where you’ll find us most Saturdays.
OVERMOUNTAIN LAND CONSERVANCY
Protected land in Ancramdale, where we live! There is an easy hike and a gazebo with great views.
HARLEM VALLEY RAIL TRAIL
Great path for walking or biking. Grab some bike rentals from our friend Sam over at Bash Bish Bicycles in Copake Falls. Reserve bikes in advance.
LITTLE APPLE CIDERY
Where our welcome party will be. Stop by for a cider tasting, picnic fare, and lawn games during the day on weekends.
BRACE MOUNTAIN
Tougher hike, if you’re up for it!
HILLROCK ESTATE
Award winning whiskey distillery with an incredible tour and tasting. Book in advance.
CHASEHOLM FARM
Farm store meets bodega attached to a dairy and creamery. Technically not an activity, but worth the trip! You haven’t lived until you’ve tried their Nimbus cheese, you won’t be sorry.
CATAMOUNT ZIP TOUR
Adventure park whose claim to fame is the longest zip line in America. Book in advance.
CATAMOUNT CABLECAR
A winter ski lift turns into a scenic joyride come summer. Views of the Taconic & Berkshire mountains.
BREAKFAST & LUNCH
RUBI’S
Cafe in Great Barrington attached to a cheesemonger. Great coffee and teas, breakfast sammies, and an extensive menu of grilled cheeses for lunch.
TWISTED SISTERS COFFEE HOUSE
Coffee shop with breakfast sammies.
COPAKE GENERAL STORE
Market and cafe with coffee, pastries, and grab-and-go sandwiches.
RANDOM HARVEST
Local organic grocer with great breakfast sammies.
THE FARMER’S WIFE
A great cafe right down the road from our house in Ancramdale.
IRVING FARM
Cafe in Millerton with solid breakfast sandwiches. Get the Fernando.
ROE JAN BREWING Co. (lunch only)
Brewery in Hillsdale with good beer and bites.
ZINNIA’s DINETTE (lunch only)
Fun fried fish joint in a diner setting with a great and eclectic selection of drinks (milkshakes, natty wine, you name it).
TOMMY B’s SLICE SHOP (lunch only)
New York style pizza with adventurous toppings.
SHOPS
HILLSDALE GENERAL STORE
Cute gift shop with great cookware and home goods. Or pop across the street to their sister store, HGS Home Chef, for kitchen supplies.
RODGERS BOOK BARN
A truly unique used book store. Very much worth a visit.
Walkable Towns to Explore
GREAT BARRINGTON 10min drive
The closest “big” town to Hillsdale. Get a taste of The Berkshires with lots of shops, restaurants, and dispensaries.
MILLERTON 15min drive
Home to Irving Farm Coffee Roasters and Harney & Sons Teas—both great breakfast or lunch spots. Great antiquing and a lovely farmers market on Saturdays.
HUDSON 25min drive
The upstate scene. Grab breakfast at Kitty’s or Mel’s bakery. Stroll down Warren Street for shopping—favorites include The Quiet Botanist, Finch, and The Social Type.