48 hours in Amenia, New York

Where to stay

Book at recently renovated Troutbeck, a historic hotel that began as a private estate and country inn in 1765. The Manor House was built in 1919 and features 17 guest rooms and suites along with a gallery, bar, and library. The elegant yet cozy accommodations offer wood-burning fireplaces and views of the expansive property which include trout pools and tennis courts. 

Day 1

Start your morning just ten minutes away at The Oakhurst Diner in nearby Millerton. The retro spot boasts a menu with French toast and omelettes along with avocado toast and the Warm Pinto Breakfast with sautéed asparagus, pinto beans, eggs, and kale chips. 

Choose your adventure: 

Slide 1 of 2
  • Option 1: Fitness

    Book a bike with Roula in advance and then hit the Harlem Valley Rail Trail. Start at Millerton Station and continue 10.7 miles south to the Wassaic Metro-North Station.

  • Option 2: Culture

    From the diner, stroll through the town of Millerton. Check out the wares at Montage Antiques or shop for chic home goods at meta44. If you're there on a Saturday, Howe recommends the farmers market.

For lunch, don't miss the Copake General Store, where you can order sandwiches (like The Serge which includes turkey, local bacon, organic pea shoots, and spicy zhug sauce or The Good Neighbor with cucumber, green pepper, tomato, and Swiss cheese) on a bed of greens. 

Less than half an hour away is your dinner destination: The White Hart Inn. There are two restaurant options: the Tap Room, where you can find British-inspired comfort food, and the more formal Dining Room, which is open on weekend nights and highlights seasonal produce sourced from nearby farms.

Day 2

Wake up early for 8 a.m. yoga at McEnroe Organic Farm. Check the schedule in advance, as classes are only offered on select dates. 

Then, refuel at the site of "the best scones in America," according to Howe. Sweet William's in Salisbury, Connecticut also serves homemade frittatas, oatmeal bowls, and other pastries along with an array of cream scones in flavors like lemon blueberry, apricot ginger, and cranberry. 

Choose your adventure:

Slide 1 of 2
  • Option 1: Fitness

    Sign up for one- or two-day fly-fishing lessons at Orvis's Millbrook, New York fly-fishing school. Learn the basics and then practice in a trout stream on the property. 

  • Option 2: Culture

    Check the showtimes and then head over to Four Brothers Drive-In Theatre for a modern take on the drive-in. Sip on a smoothie or fresh Lucy Juicy juice (carrot, orange , ginger, and parsley) while you watch. 

Have lunch al fresco at McEnroe Organic Farm. Try the Bulgarian salad with grilled chicken, cucumber, bell pepper, mixed greens, and feta-herb vinaigrette. If you're looking for something heartier, go for the Caprese sandwich with McEnroe's own tomatoes.  

Stroll the ample wilderness that surrounds Troutbeck to work up an appetite for dinner. Follow the Webutuck River over Stone Bridge past Delamater House then circle back upwards and cross Wood Bridge. If you like, stop by the on-site courts for a game of tennis or, weather-permitting, jump in the pool. 

Like many of the area's chefs, Troutbeck's executive chef Gabe McMackin prioritizes ingredients from local farms. Sample composed dishes like fennel, roasted and raw with buttermilk and wood sorrel, roasted tilefish with peas, turnips, and mussels, and citrus salad with castelfranco, pistachio, and saba.

Bid goodbye to your adventure with a nightcap at the bar.

48 hours in Milan

There are over 100 miles of cycling paths inside the city.