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Let’s make this your best trip ever. We want you to venture beyond the four walls of our homes to explore everything each destination has to offer. From amazing restaurants, to outdoor activities, to local treasures around Wander Berkshires Retreat. Continue below to view our local activity guide video, travel guides, restaurant recommendations and more.

Explore this location

Welcome to New Marlborough, Massachusetts

Near East Hill Road in New Marlborough, Massachusetts, there are plenty of activities to enjoy in the heart of the Berkshires. Outdoor enthusiasts can explore nearby hiking trails, including those at Beartown State Forest, perfect for nature walks, birdwatching, and picnics. The area is also known for its charming farms and local markets. For a cultural experience, visit nearby Great Barrington for art galleries, local theaters, and farm-to-table dining. Skiing and fishing are popular seasonal activities.

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Travel guides

Let's make this your best trip ever

Some details may change as Wander updates our homes and operations. Wander Concierge is at your service with any questions.

Restaurants

Fine dining with beautiful views

Cantina 229

An inviting farm-to-table restaurant, offering seasonal, globally-inspired dishes plus craft cocktails in a casual setting with lawn games, bonfires, and community-style or private seating. Reservations may be booked through Resy. Open 5 PM - 9 PM, Thursday-Sunday; closed Monday-Wednesday.

The Old Inn On The Green Restaurant

An intimate, historic inn offering a prix fixe menu with seasonal, locally sourced dishes crafted by Chef Peter Platt along with an extensive wine list. Guests can dine by candlelight in cozy, restored rooms or enjoy the canopied garden terrace in warmer months. Reservations can be made through OpenTable. Open 5:30 PM - 9 PM, Wednesday-Sunday; closed Monday-Tuesday.

Number Ten

A classic steakhouse in Great Barrington serving American and French favorites with a focus on locally sourced, sustainable ingredients. Diners can relax in the inviting dining room or lively bar, featuring an extensive American whiskey selection and live jazz. Open 5 PM - 8:30 PM daily.

Activities

Butternut Ski Area and Tubing Center

A family-friendly ski resort with over 10 acres of runs, 11 lifts, and artificial snowmakers on all trails, offering skiing, snowboarding, and tubing. Its popular Tubing Center features up to 10 lanes, hundreds of tubes, a Magic Carpet Lift, and 100% snow-making coverage, making it a top destination for tubing in New England. Hours vary seasonally.

Ashintully Gardens

An elegant blend of formal and natural landscapes, this tranquil Berkshires destination features sculptures, winding paths, and serene garden rooms. Open from dawn to dusk daily.

Les Trois Emme Vineyard & Winery

An inviting family-owned winery, offering tastings in a cozy setting in New Marlborough. Named after the owners' granddaughters, the winery features a selection of wines crafted on-site.

Groceries

Stop & Shop

This supermarket chain has house-brand groceries and organics, plus deli and bakery counters. Open 7 AM - 10 PM every day except Sundays (closes 9 PM).

Big Y World Class Market

An American, family-owned supermarket chain throughout Massachusetts and Connecticut. Open 7 AM - 9 PM daily.

Berkshire Food Co-Op

An inclusive, accessible store that sells local, sustainable, and organic grocery essentials. Open 8 AM - 7 PM daily.

THE WANDER APP

The best activities, in your pocket

Soon, we’re rolling out Wander Explore, giving you access to the best destinations during your trip. Download the app today to get notified when we launch.

Wander Explore
Coming soon

Explore all the best restaurants, museums, trails, parkings, pharmacies, and more. Save your favorite picks, create lists, make reservations - all from the Wander app.

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Wander Berkshires Retreat: Transportation Guide

Wander Berkshires Retreat: Restaurant Guide