Tobey & Chris
Tobey & Chris
Things to Do
Nearby Hikes
Appalachian Train - Lions Head to Bear Mountain
Difficulty: Moderate
Length: 8.2 mi
Elevation gain: 1,594 ft
Route type: Out & back
Difficulty: Moderate
Length: 3.6 mi
Elevation gain: 1,013 ft
Route type: Out & back
Difficulty: Moderate
Length: 0.9 mi
Elevation gain: 101 ft
Route type: Out & back
Difficulty: Moderate
Length: 6.1 mi (can do shorter out and back)
Elevation gain: 1,683 ft
Route type: Loop
Difficulty: Hard
Length: 3.6 mi
Elevation gain: 1,509 ft
Route type: Out & back
Other Outdoor Activities
- Highest waterfall in MA
- Short walk to falls
- 24 acres of land and gardens
- Stockbridge, MA
Swim at Rudd Pond
- Local pond with beach and fishing
Golf at Hotchkiss
- Play 9 or 18 Holes
- Open to public after 11am
Bike the Harlem Valley Rail Trail
- 26 miles from Wassaic to Copake Falls
- Recently expanded and paved through farmlands and towns
Swim or Canoe at Lake Wononscopomuc
- Boat rentals available at public lake
Indoor/Town Activities
Visit Edith Wharton's The Mount
- Historical landmark home of Edith Wharton in Lenox, MA
- Group and ghost tours available
- Fun museum in Stockbridge, MA
- Timed tickets highly encouraged
- Culture and dance center in Becket, MA
- Outdoor performances offered
- Gilded Age Estate in Stockbridge, MA
- House and garden tours available
Visit Millerton, Great Barrington, Stockbridge, or Lenox
- Great shopping, antiquing, art galleries, and bookstores
- See below for recommended restaurants
Where to Eat
Millerton, NY
Four Brother's Pizza - locally owned Greek pizza spot with the best Greek salad dressing around!
Oakhurst Diner - Fun, retro diner with comfort food and an updated menu, great breakfast or burger spot!
Irving Farm - Outpost of the East Village cafe (Tobey was devastated when she found out it was an NYC chain) with good sandwiches, coffee, and baked goods
Millerton Inn - Upscale lunch and dinner spot with American classics with a Mediterranean spin
52 Main - Lively tapas restaurant with a fun bar and small plates - ask Jeff Bakkensen if you need an explanation about this type of cuisine
Harney & Sons - Local tea purveyor with a cafe and tours of their tea factory - the mother of the bride orders their tea bags in giant bulk bags!
Lakeville, MA
The Woodland Restaurant - upscale restaurant in a beautiful old house with an ever-changing menu - located in a cell phone dead spot so if you plan on meeting people here, plan ahead!
Mizza's Pizza - delicious local pizza joint and the only people willing to put up with delivering food miles up a dirt road and allowing a bunch of barely-bathed mountain folk watch World Cup soccer on a regular basis
The Boathouse - nautically-themed seafood spot with good cocktails and a fantastic sushi chef
Black Rabbit - local bar and grille with American cuisine and sandwiches
Picante's - casual Mexican spot with margarita pitchers
Salisbury, CT
The White Hart Inn - upscale and cozy hotel bar/inn with a great porch and lawn - perfect for delicious drinks from their appropriately too-cool bartender
Provisions - Sandwich shop and cafe located in the White Hart Inn - great for to-go sandwiches and meals!
Neo - Italian and American cuisine with everything from burgers, to flatbreads, to pasta
Sweet William's - cafe and bakery for desserts and morning baked goods
Amenia, NY
Serevan - upscale Mediterranean restaurant in an antique farmhouse where our favorite chef - Serge, grows his own vegetables and herbs. Our go-to for mountain anniversary date nights!
Four Brother's Pizza - locally owned Greek-style pizza spot with great ice cream and shakes. Fun fact - bridesmaid Abby Moore worked there last summer!
A Little further, but worth the drive
SoCo Creamery, Great Barrington, MA - amazing ice cream and Father of the Bride's favorite black and white shake!
Red Lion Inn, Stockbridge, MA - fun covered porch with rocking chairs in a bucolic setting - perfect for drinks!
Great Barrington Bagel, GB, MA - this place sold their everything bagel crumbs even before TJ's did!
Big Elm Brewing, Sheffield, MA - craft beer brewhouse with a fun taproom
Berkshire Mountain Distillers, Sheffield, MA - local distillery with a tasting room
The Prairie Whale, Great Barrington, MA - trendy, local, farm to table restaurant