Ultimate Berkshires Travel Guide: Visiting The Berkshires & Best Hotels in Lenox MA
- Ryan Jones
- Mar 28
- 5 min read
Introduction to Visiting The Berkshires
The Berkshires region in western Massachusetts is a beloved New England destination famous for its picturesque landscapes, vibrant culture, and charming towns. Renowned for spectacular fall foliage, visiting the Berkshires in autumn provides an unforgettable visual feast. Beyond the colorful scenery, visitors will discover historic sites, farm-to-table restaurants, world-class museums, and thriving arts venues. Whether you're planning a romantic weekend, family trip, or solo retreat, the Berkshires offer experiences that cater to every type of traveler.
Though beautiful year-round, the Berkshires particularly shine during fall. Peak foliage typically occurs in early to mid-October, when trees turn vibrant shades of red, orange, and gold. This period also aligns with numerous seasonal festivals and events that showcase local culture, food, and arts, making autumn a prime time to visit.
Exploring Lenox, Massachusetts: A Gem of The
Berkshires
Lenox is one of the most captivating towns in the Berkshires, known for its historic charm, cultural depth, and scenic beauty. A hub for art and culture enthusiasts, Lenox hosts Tanglewood, the renowned summer home of the Boston Symphony Orchestra, attracting visitors from around the globe. Its quaint downtown streets lined with boutique shops, cozy cafés, and historic buildings provide a perfect backdrop for leisurely exploration.
In addition to cultural attractions, Lenox boasts proximity to stunning hiking trails, including the famous Monument Mountain and Mount Greylock. The town’s prime location and range of accommodations make it an ideal base for those visiting the Berkshires.
Best Hotels in Lenox MA
Luxury Hotels & Resorts in Lenox
Nestled on a sprawling 110-acre estate, Blantyre offers a luxurious escape in a beautifully renovated Tudor Revival mansion. Guests experience classic elegance coupled with modern comforts in rooms that blend traditional decor with contemporary amenities. The hotel’s Conservatory restaurant offers refined dining with an exquisite menu featuring seasonal ingredients. Blantyre’s charm lies in its thoughtful details, historic ambiance, and unmatched service, ideal for special occasions or a romantic getaway.
Boutique Inns & Bed-and-Breakfasts in Lenox
The Inn at Kenmore Hall provides guests a stylish, intimate experience. Formerly a boarding school and later a guesthouse frequented by musicians like Leonard Bernstein, this historic property has been transformed into a chic bed-and-breakfast by its current owners, Frank Muytjens and Scott Edward Cole. Rooms boast contemporary design and luxurious touches, like vintage furnishings and plush bedding, complemented by personal hospitality, including breakfast served by candlelight.
Another elegant boutique B&B in Lenox, 33 Main, offers a blend of upscale comfort and historic charm. Centrally located, this inn makes exploring Lenox’s attractions and dining scene incredibly convenient. Guests enjoy beautifully designed rooms, gourmet breakfasts, and personalized service that enhances the intimate atmosphere of this upscale retreat.
Affordable & Family-Friendly Hotels in Lenox
The Constance is a welcoming, budget-friendly hotel located conveniently near downtown Lenox. Ideal for families, it features comfortable accommodations, a cozy fireplace lounge area, and proximity to many attractions, shops, and restaurants. It's the perfect balance of affordability, location, and family-oriented amenities.
Life House Berkshires presents a modern twist on the classic American roadside motel, transformed into a chic accommodation with updated rooms featuring luxurious touches like Le Labo toiletries. Its stylish lobby and bar, known as The Club Room, offer guests a cozy and sophisticated place to unwind after exploring the Berkshires.
Things to Do When Visiting The Berkshires
Outdoor Activities & Adventure
From hiking to ziplining, outdoor adventures abound in the Berkshires. Monument Mountain offers stunning summit views and moderate hiking trails, while Mount Greylock provides more challenging paths to Massachusetts’ highest peak. Ramblewild in Lanesborough presents an exhilarating aerial adventure park with rope courses and zip lines, suitable for visitors of all ages and fitness levels.
Explore World-Class Museums
Art and culture enthusiasts visiting the Berkshires cannot miss The Clark Art Institute, renowned for its extensive collection of Impressionist art, serene grounds, and reflective pools. MASS MoCA in North Adams complements this cultural experience with massive contemporary installations, music festivals, and innovative exhibits.
Historic Sites & Cultural Experiences
Immerse yourself in history and culture by visiting Tanglewood for memorable concerts beneath the stars, Hancock Shaker Village for insights into Shaker life and traditions, and The Mount, the beautifully preserved home of famed writer Edith Wharton.
Best Dining in The Berkshires: Farm-to-Table & Fine
Dining
Dining in the Berkshires emphasizes fresh, local ingredients showcased through innovative and comforting dishes. Cantina 229 in New Marlborough delivers an exceptional farm-to-table experience with dishes that blend global flavors creatively. The Prairie Whale in Great Barrington similarly offers seasonal, locally sourced American cuisine in a relaxed, hip atmosphere.
For a fine dining experience with historic ambiance, The Old Inn on the Green is unmatched. Its candlelit dining rooms and French-inspired American cuisine create a memorable experience. Blantyre’s Conservatory Restaurant in Lenox is another luxurious option, serving refined dishes in an elegant glass conservatory.
Shopping & Antiquing in The Berkshires
The Berkshires offer abundant opportunities for unique shopping experiences, particularly antiquing. Towns like Great Barrington, West Stockbridge, and Lenox boast charming boutiques, antique stores, and local artisan markets. Popular spots include Rubiner’s cheese shop, Sandy Klempner’s antique treasures, and Charles H. Baldwin & Sons for local spices and extracts.
Seasonal Events & Festivals in The Berkshires
Visiting during fall means enjoying renowned seasonal events such as the Naumkeag Pumpkin Show, showcasing thousands of jack-o-lanterns, and the Berkshire Botanical Garden Harvest Festival, which celebrates local crafts, food, and agriculture. The Lenox Apple Squeeze is another fall highlight, drawing crowds with everything apple-related, from cider donuts to apple pies.
Practical Travel Tips for Visiting The Berkshires
Getting to The Berkshires
Located conveniently for travelers from Boston and New York City, the Berkshires are about a two-and-a-half-hour drive from each city. Consider flying into Boston Logan or Albany International Airport, then renting a car for the scenic drive.
What to Pack
Prepare for outdoor activities with sturdy shoes, layered clothing, and weather-appropriate gear. In autumn, pack cozy sweaters, jackets, and hiking boots to fully enjoy foliage adventures.
Budgeting for Your Trip
Accommodations range from affordable inns starting around $150 per night to luxury resorts upwards of $600 per night. Dining also varies widely, with casual meals averaging $15-25 per person and fine dining experiences at $50 or more per person. Planning ahead can help secure the best rates and availability.
Final Thoughts: Why Visit The Berkshires
The Berkshires provide a perfect blend of cultural depth, outdoor adventures, world-class dining, and cozy accommodations. Whether visiting for the scenic beauty, artistic experiences, or culinary delights, travelers will find endless reasons to return. Start planning your Berkshires escape today and discover why it's one of New England’s most cherished destinations.
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