35 Things To Do in Lenox

Nestled in the heart of the Berkshires, Lenox, Massachusetts, invites visitors to explore its rich history, vibrant arts scene, and stunning natural beauty. Known for its picturesque landscapes and cultural landmarks, this charming town offers a perfect blend of outdoor adventures and artistic experiences.

Whether you’re a nature enthusiast eager for scenic hikes or an art lover looking to discover unique galleries and performances, Lenox boasts diverse attractions that cater to all interests. Full of quaint streets and welcoming spots, the town promises an unforgettable experience for travelers.

The Mount, Edith Wharton’s Home

Our Rating: 9.0/10

The Mount is a stunning example of early 20th-century design. Crafted by the renowned author Edith Wharton herself in 1902, it is a National Historic Landmark and a vibrant cultural center. Visitors can explore the house through guided and self-guided tours, immersing themselves in Wharton’s world. The enchanting gardens offer a peaceful escape amidst the beautifully landscaped grounds.

Events like live music and outdoor sculpture exhibits fill the calendar, ensuring there’s always something new to discover at The Mount. This charming estate is a must-see destination whether you love architecture, literature, or history.

Pleasant Valley Wildlife Sanctuary

Our Rating: 8.7/10

Pleasant Valley Wildlife Sanctuary is a nature lover’s paradise. With over 1,000 acres, it offers lush forests, colorful meadows, and diverse wetlands. Visitors can explore trails that wind through these stunning landscapes. Nature enthusiasts will find seven miles of trails, perfect for leisurely walks or more challenging hikes. Each path is well-marked and offers a chance to immerse in the serene beauty of the Berkshires.

Families will delight in the variety of outdoor programs. From wildlife watching to discovering beaver lodges, there’s something for everyone. The sanctuary offers a peaceful retreat and an escape into nature’s wonders.

Canyon Ranch

Our Rating: 8.5/10

Canyon Ranch offers a transformative experience for visitors seeking wellness and relaxation. Each day, guests can choose from over 40 different classes and activities. They can start their morning with invigorating hikes through scenic trails or try calming tai chi sessions. Canyon Ranch provides world-class spa treatments for those inclined towards self-care.

Visitors can indulge in massages that melt away stress or learn meditation techniques for peace of mind. Guests interested in health education can attend enlightening lectures on bone health and nutrition. Whether seeking physical renewal or mental tranquility, Canyon Ranch provides a sanctuary for discovery and rejuvenation.

Kennedy Park

Our Rating: 9.2/10

Kennedy Park is a haven, especially for those who love the outdoors. Spanning over 500 acres, it provides countless hiking trails winding through beautiful hardwood forests. In winter, the park transforms into a snowy wonderland perfect for cross-country skiing and snowshoeing. The trails are well-marked, making navigation easy even for beginners.

Families and friends can enjoy picnics at the scenic Overlook, with views that make every moment memorable. Whether a stroll or an adventurous bike ride, Kennedy Park promises unforgettable natural experiences.

Ventfort Hall Mansion and Gilded Age Museum

Our Rating: 8.5/10

Ventfort Hall Mansion and Gilded Age Museum is a stunning Jacobean-Revival mansion that transports visitors back to the opulent days of the Gilded Age. This architectural marvel offers an insightful peek into American society at the turn of the century. Guests can explore beautifully restored rooms brimming with period furnishings and intricate woodwork. Engaging tours reveal the fascinating stories of the elite who once lived in this grand estate.

The museum hosts a variety of exhibits and events throughout the year. These include children’s story hours and captivating seasonal performances that enrich the visitor experience. Ventfort Hall is an essential stop for history buffs and lovers of classic architecture.

Norman Rockwell Museum

Our Rating: 9.1/10

The Norman Rockwell Museum offers a glimpse into America through the eyes of one of its most beloved artists. The museum houses the most extensive collection of Rockwell’s original art. Visitors can wander through galleries displaying iconic paintings that vividly capture everyday life.

The experience extends beyond the art. Rockwell’s studio, open from May to October, invites exploration of the space where he created his masterpieces. The serene Terrace Café offers a spot to relax and reflect. Whether you’re an art enthusiast or just curious, the museum promises a captivating journey through one artist’s vision of American life.

Shakespeare & Company

Our Rating: 9.3/10

Shakespeare & Company offers a captivating journey into the world of theater. This venue presents Shakespeare’s timeless plays and contemporary works, ensuring diverse performances. Visitors can immerse themselves in the arts with outdoor shows set against stunning meadows. The tranquil setting enhances the magic of live theater.

Guests are encouraged to explore the nearby quaint shops and eateries, rounding out a day of culture and leisure. This theater is not just about watching plays. The company holds free educational programs, fostering a deeper appreciation for the arts. Whether a theater enthusiast or a casual visitor, Shakespeare & Company promises a memorable experience.

Frankie’s Restaurant

Our Rating: 8.7/10

Frankie’s Restaurant offers a warm and inviting taste of Italian-American cuisine. With family roots and a focus on authentic flavors, it serves dishes “like your Mamma used to make.” Whether dining inside or enjoying the fresh air on their outdoor patio, visitors are treated to delicious meals crafted with care.

The restaurant provides options for everyone, including vegan selections and convenient takeout. Guests can enjoy mouth-watering pasta, pizzas, and a welcoming atmosphere that feels like home.

Haven

Our Rating: 8.7/10

Haven is a cozy café and bakery. It’s the perfect spot to start your morning with freshly baked pastries and expertly brewed coffee. Visitors often rave about the warm atmosphere and the delicious aromas that greet you as you walk through the door.

Breakfast at Haven is a must-do. Enjoy classic dishes with a creative twist made from locally sourced ingredients. The outdoor seating area provides a charming spot to enjoy your meal on a sunny day, making it a delightful, relaxing haven. Haven is not just a stop; it’s a destination, promising a memorable culinary experience.

The Olde Heritage Tavern

Our Rating: 8.5/10

The Olde Heritage Tavern invites guests with its welcoming charm and lively atmosphere. This local favorite is perfect for those seeking classic comfort food. The menu features juicy burgers and savory wings, making it a go-to spot for a satisfying meal.

Visitors can catch up with friends over drinks while watching the latest sports game on big screens. The tavern’s warm and friendly environment makes it a popular destination to unwind after a long day exploring the town. Enjoy a relaxed evening surrounded by locals and experience the community spirit that defines Lenox.

Wyndhurst Golf & Club

Our Rating: 8.3/10

Nestled in the scenic Berkshires, Wyndhurst Golf & Club offers a historic 18-hole course with breathtaking views. Golfers of all skill levels can enjoy the challenge of this beautifully maintained course while soaking in the lush surroundings.

Beyond golf, Wyndhurst features several other activities. Visitors can unwind in the refreshing swimming pool or work on their swing at the indoor golf simulator. The club’s fitness center caters to those who love to stay active, providing modern equipment in a serene setting.

The Center at Lenox

Our Rating: 8.5/10

The Center at Lenox is the beating heart of this charming Massachusetts town. Visitors can stroll through quaint streets lined with unique shops and cozy cafes. The town center has an inviting, high-end vibe and a warm, local feel.

Art lovers can explore galleries showcasing captivating works by local artists. The lively atmosphere makes it perfect for leisurely walks and spontaneous discoveries. Tasting local specialties at delightful bistros adds to the vibrant experience. The Center is not just about shopping and dining. It’s a place to immerse oneself in the town’s rich culture, savoring its historic charm and modern allure.

Undermountain Farm

Our Rating: 8.5/10

Undermountain Farm offers a captivating experience for anyone who ventures to this scenic spot. Horseback riding through 150 acres of lush forests, meadows, and pastures is unmatched in charm. Riders can lose themselves in the serene beauty of Western Massachusetts as they trot along trails with breathtaking mountain views.

This farm is friendly to all skill levels. Whether you are an expert equestrian or a beginner, the gentle horses and expansive landscape make for a delightful outing. Visitors can also enjoy year-round riding thanks to a spacious indoor arena, making the farm appealing in every season. It’s a perfect spot for individuals and families looking to connect with nature and enjoy a unique adventure.

Lenox Library

Our Rating: 8.5/10

The Lenox Library is a cultural cornerstone. This charming library offers a blend of historical architecture and modern amenities. Visitors can explore its rich collections, including rare books, music, and local history. The library transforms into a vibrant hub with public-access computers and exciting programs for all ages.

Artwork lines the walls, creating an inspiring environment. Frequent art exhibitions invite patrons to enjoy and discover new talents. The library provides guided tours for those interested in history that delve into Lenox’s past. Whether seeking a quiet reading spot or an engaging cultural experience, the Lenox Library is a must-visit destination.

Hilltop Orchards

Our Rating: 8.7/10

Hilltop Orchards is a must-visit for anyone. Here, visitors can immerse themselves in a range of delightful experiences. Strolling along scenic hiking trails offers breathtaking views of the Berkshire landscape, perfect for a relaxing adventure.

The warmth of the orchard’s atmosphere is complemented by their artisanal craft apple ciders and wines. You can savor these local specialties while relaxing by a cozy fire. Their fresh, spiced apple cider donuts are a fall favorite, making them an irresistible treat. Whether it’s the allure of a nature hike or the allure of hand-crafted beverages, Hilltop Orchards provides a charming setting for unforgettable moments.

Elayne P. Bernstein Theatre

Our Rating: 8.5/10

Tucked away in the beautiful Berkshires, the Elayne P. Bernstein Theatre offers an intimate experience. Visitors are drawn in by its cozy setup, with the audience close to the stage, feeling every moment of the performance. It’s like stepping into another world where Shakespeare’s works and contemporary plays come alive.

Each show at the theater is a chance to see top-notch acting and stagecraft. The setting makes everyone feel like they are part of the story. People often leave with new perspectives and unforgettable memories. Seeing a performance here isn’t just watching a play, it’s living it.

Koussevitzky Music Shed

Our Rating: 8.7/10

The Koussevitzky Music Shed is a must-visit for music lovers in Lenox, Massachusetts. Famous for its excellent acoustics, the venue hosts performances by the Boston Symphony Orchestra and other talented musicians.

Arriving early is key to soaking in the vibrant atmosphere. Enjoy a relaxing picnic on the lawn before the concert begins. Seating options inside the shed provide a closer view of the stage, adding to the immersive experience. With its lush surroundings, the shed offers more than just music. The scenic views and serene environment make for a perfect day or evening outing in the Berkshires.

Elm Court Estate

Our Rating: 9.1/10

Elm Court Estate is a splendid showcase of Gilded Age opulence. Vast and luxurious, the estate invites visitors to explore its elegant architecture and grand gardens. Surrounded by the stunning landscapes of the Berkshires, Elm Court offers a picturesque setting for anyone looking to experience historical charm.

Guests can enjoy strolls through its meticulously maintained gardens. Take in the beauty of the architecture, which echoes a time of grandeur. Inside, the mansion’s history whispers through ornate decorations and stately rooms, making every visit memorable. Whether you’re a history enthusiast or a beauty lover, Elm Court Estate offers a unique journey back in time.

Alta Restaurant

Our Rating: 9.3/10

Alta Restaurant & Wine Bar offers an unforgettable dining experience. Visitors are drawn to its vibrant atmosphere and warm hospitality. The menu boasts a selection of Mediterranean-inspired dishes crafted with local and organic ingredients. Diners can savor meals that highlight fresh, seasonal flavors, making each visit a delightful culinary adventure.

The extensive wine list features selections from around the world. This makes Alta a perfect spot for wine enthusiasts to discover new favorites while enjoying carefully paired meals. The charming ambiance and attentive service make it a must-visit spot for locals and travelers.

The Bookstore and Get Lit Wine Bar

Our Rating: 8.7/10

The Bookstore and Get Lit Wine Bar is a local treasure. Visitors can browse through an eclectic mix of new and second-hand books, finding gems that fit their unique tastes. It’s the perfect spot for those who enjoy curling up with a good read.

Beyond the books, the wine bar offers an inviting atmosphere to unwind. Featuring a selection of fine wines, it’s an excellent place to relax with friends or enjoy quiet time. Whether sipping a glass of wine or getting lost in a thrilling novel, this cozy spot promises a memorable experience.

The Wit Gallery

Our Rating: 8.5/10

The Wit Gallery is a must-visit destination for art enthusiasts. Nestled in the heart of Lenox’s historic downtown, this gallery showcases a vibrant collection of contemporary art.

Visitors can explore a diverse range of artwork from both well-known and emerging artists. The space features installations in various media, offering something for everyone. Whether you’re a seasoned collector or just beginning your art journey, The Wit Gallery invites you to immerse yourself in creativity and inspiration.

Trinity Episcopal Church

Our Rating: 8.5/10

Trinity Episcopal Church offers a glimpse into the spiritual and architectural beauty of a Gilded Age setting. Visitors enter a space filled with striking woodcarvings and stunning stained glass windows. The church is a historical marvel and a vibrant community hub. People gather for worship, reflecting the warm and inclusive spirit of the congregation.

For those looking for a place of peace, the church is open daily for prayer and meditation. Its serene atmosphere is an ideal spot to pause and reflect amidst your travels in Lenox.

Miraval Berkshires Resort and Spa

Our Rating: 8.6/10

Miraval Berkshires Resort and Spa offers an escape into a world of relaxation and mindfulness. Set in the beautiful Berkshires, it invites guests to unwind in a serene setting with various wellness experiences. Visitors can start their day with yoga classes on peaceful grounds or try a unique meditation session to refresh their minds.

Art workshops provide a perfect outlet for those looking to engage their creative side. The resort ensures something for everyone, offering culinary classes that delve into healthy cooking and nutrition. The Life in Balance Spa provides various treatments to rejuvenate body and spirit. Each experience at Miraval is crafted to promote a sense of well-being and tranquility.

Garden Gables

Our Rating: 8.6/10

Garden Gables Inn is a charming retreat nestled on five lush acres. Visitors are treated to a blend of historic charm and modern luxury. The inn offers private seating for breakfast and a farm-to-table experience. Guests enjoy locally sourced treats crafted to perfection.

In warmer months, the heated Olympic-size pool invites relaxation under the sun. During the renowned Tanglewood season, Garden Gables becomes a prime spot for music lovers, offering easy access to the festivities. Each visit provides a chance to unwind and soak in the tranquil ambiance of the Berkshires.

Firefly Gastropub

Our Rating: 8.7/10

Firefly Gastropub is a vibrant spot. It offers high-quality comfort food in a cozy setting. Visitors can enjoy an ever-changing craft beer menu and creative cocktails. The friendly and welcoming atmosphere makes it a great place to relax with friends.

The menu features both classic pub fare and seasonally curated specials. Each dish is made with care, ensuring a delightful dining experience. Regular events, such as live music nights, add an extra touch of excitement. You can unwind with the sounds of rhythm and blues while savoring your meal. Firefly Gastropub is a must-visit for those looking to enjoy great food and lively entertainment.

Blantyre

Our Rating: 9.3/10

Blantyre is a stunning Gilded Age estate nestled in the scenic landscape. Visitors can explore the impressive 117-acre property, which offers breathtaking views and a serene escape from city life. The estate’s charming architecture invites guests to step back in time. Each room exudes elegance and comfort, making it an ideal retreat.

Outdoor enthusiasts will love the estate’s picturesque walking trails. The grounds transform into a wonderland for snowshoeing and cross-country skiing in winter. Indulge in fine dining at Blantyre’s exquisite restaurant. The menu features gourmet dishes that highlight local ingredients. Dining here promises a memorable culinary experience. Relaxation seekers can unwind at the on-site spa. Treat yourself to a variety of rejuvenating services, including massages and facials.

Lenox Club

Our Rating: 8.5/10

The Lenox Club captures the essence of elegance and leisure in the Berkshires. Nestled amidst rolling hills and lush landscapes, this historic venue offers a unique blend of relaxation and recreation. Visitors can enjoy a round of golf on the beautifully manicured course, surrounded by stunning natural vistas. The club hosts lively social events and provides fine dining experiences with locally sourced ingredients.

In colder months, the Lenox Club becomes a cozy retreat where guests can warm up by the fireplace and savor a delightful cup of cocoa. Whether you’re seeking adventure or tranquility, the Lenox Club promises a memorable escape every season.

Lenox Coffee

Our Rating: 8.3/10

Nestled on Main Street, Lenox Coffee is a charming spot perfect for a morning pick-me-up or an afternoon break. The aroma of freshly brewed coffee greets visitors, inviting them to relax with a crafted latte or a delicious pastry.

Customers can enjoy their drinks indoors or soak up the sun outside when the weather is pleasant. With its cozy seating and inviting ambiance, Lenox Coffee offers the perfect escape from the bustle of daily life.

Tanglewood

Our Rating: 9.5/10

Tanglewood is a music lover’s paradise. Nestled in the scenic Berkshires, it is home to the Boston Symphony Orchestra during the summer. Concertgoers can enjoy performances under the stars, where the sounds of classical symphonies fill the crisp evening air.

The grounds of Tanglewood are perfect for picnicking. Visitors can spread a blanket on the lush lawns, surrounded by the natural beauty of the trees and hills. This setting provides a peaceful backdrop for enjoying music and the tranquility of nature. Throughout the summer, Tanglewood offers a schedule of concerts featuring world-class musicians and diverse genres, including classical, pop, and jazz, ensuring something for everyone.

Sloane’s Tavern

Our Rating: 7.5/10

Sloane’s Tavern offers a charming escape with delightful dining experiences. Nestled at 55 Lee Rd, it greets visitors in spring, summer, and fall with a relaxed atmosphere. Guests can savor a variety of light fare paired with a wide array of imported and domestic beers.

The tavern sits near the beautiful Wyndhurst golf course, providing picturesque views that guests can enjoy while sipping their drinks. Though sometimes busy, the tavern offers a great spot for winding down after a day exploring Lenox’s attractions.

Tom Fiorini Artist

Our Rating: 8.5/10

Tom Fiorini’s Sculpture Yard is a hidden gem for art enthusiasts. Visitors are greeted by striking metal and chainsaw sculptures showcasing Fiorini’s unique creativity and skill. Wander through the garden to discover whimsical works. From clever signs to junk metal horses, there is always something intriguing to catch your eye.

Tom is often present, sharing stories and insights about his art and Lenox’s history. Engaging with him adds a personal touch to the experience, making each visit memorable and enlightening. Fiery passion for his craft shines through, captivating all who venture into his artistic haven.

Bistro Zinc

Our Rating: 8.7/10

Bistro Zinc exudes an air of casual elegance. This charming restaurant offers a delightful experience with its warm ambiance and attentive service. Visitors can taste culinary masterpieces like crispy goat cheese salad or exquisite trout topped with crab meat.

With its inviting atmosphere, the bistro is a perfect spot for intimate dinners and lively gatherings. Classical French tunes play softly in the background as diners savor flavorful dishes. Exploring the locally inspired menu is tempting, making Bistro Zinc a standout destination for food lovers.

Berkshire Athenaeum

Our Rating: 8.5/10

The Berkshire Athenaeum is a haven for lovers of books and history. Visitors can explore its vast collection of literature and historical archives. The library hosts regular events, including author talks and workshops, making it a lively spot for community engagement.

Art enthusiasts will appreciate the rotating exhibits showcasing local artists. The serene reading rooms offer a perfect escape for those seeking a quiet retreat. Whether you’re delving into a book or attending an event, the Athenaeum provides a rich cultural experience.

Nejaime’s Wine Cellars

Our Rating: 8.6/10

Nejaime’s Wine Cellars is a beloved spot where wine enthusiasts can explore an impressive array of wines from across the globe. The shop’s extensive selection features about 2,000 different varieties, ensuring there is something for every palate.

Visitors can enjoy complimentary tastings every Saturday afternoon. It’s a delightful way to discover new favorites in a friendly and welcoming atmosphere.

With over 40 years of history, Nejaime’s is more than just a store. It’s a place to experience the warmth of the Berkshires, whether shopping for spirits or engaging in lively weekend events.

Chocolate Springs Cafe

Our Rating: 9.2/10

Chocolate Springs Cafe is a sweet oasis for any chocolate lover. Visitors can indulge in gourmet European-style desserts crafted with exquisite detail. The cafe boasts an inviting atmosphere with its cozy seating and live music, making it the perfect spot to relax and enjoy.

Satisfy your sweet tooth with freshly made chocolates, cakes, and gelato. The cafe is also famous for its award-winning hot chocolate, a must-try for anyone visiting. For those needing a caffeine kick, the cafe offers a variety of espresso drinks and teas. Under the talented guidance of Chocolatier Joshua Needleman, Chocolate Springs Cafe promises a delightful culinary experience you won’t forget.

Lenox offers a delightful array of activities that cater to every taste, whether seeking serene nature trails, rich cultural experiences, or cozy eateries. So pack your bags and set your sights on Lenox, where unforgettable memories await at every corner.