Discovering The Best Things to do in Lenox MA

Looking for the fun and best things to do in Lenox MA? Lenox is a charming town in Massachusetts that offers a wide range of outdoor activities and beautiful green spaces. It is best known for its serene atmosphere, Tanglewood Music Festival, and summer concerts. If you’re seeking tranquility, Lenox is the ideal destination.

This small yet vibrant town is a haven for outdoor enthusiasts, with its majestic green spaces and opportunities for outdoor fun. You can immerse yourself in the serenity of parks and mountains, while also enjoying live music performances at summer concerts and the renowned Tanglewood Music Festival. 

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If you’re interested in delving into the town’s history, you can explore its libraries and museums. Lenox promises an unforgettable vacation for your family and loved ones. Whether you want to experience the calm of nature, indulge in musical delights, or delve into the town’s rich history, Lenox is the perfect place for an unforgettable trip. 

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Here are the best things to do in Lenox MA:

1.  Sohn Fine Art

Sohn Fine Art

One of the best things to do in Lenox MA is to visit Sohn Fine Art, which was founded in 2012 by Cassandra Sohn, a renowned photographer. This gallery specializes in contemporary photography and is dedicated to promoting, exhibiting, and nurturing the work of local and international artists. In addition to showcasing stunning photography, Sohn Fine Art actively contributes to community development by hosting art exhibitions, workshops, and lectures. 

Notably, the gallery organizes an annual Master Artist Series program, inviting world-famous photographers to share their expertise and experiences with professionals and aspiring photographers, as well as collectors of photography. If you have a passion for photography or simply appreciate captivating visuals, a visit to Sohn Fine Art is a must-do activity when exploring Lenox, MA.

Address: 69 Church St, Lenox, MA 01240, United States

2. Berkshire Horseback Adventures

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Berkshire Horseback Adventures

One of the top attractions in Lenox, MA that should definitely be on your list of the best things to do is Berkshire Horseback Adventures. This exciting destination draws in horse riders of all levels, making it a must-visit spot for equestrian enthusiasts looking to enhance their riding skills. It’s also a fantastic place for a family outing, offering an enjoyable experience and an opportunity to spend quality time together. 

As you embark on your adventure with the magnificent horses, you’ll be treated to breathtaking and picturesque views that are truly extraordinary. Don’t forget to bring your camera along to capture stunning photos to share on your Instagram feed. Rest assured, the horses at Berkshire Horseback Adventures are well cared for, healthy, and highly sought after.

Address: 293 Main St, Lenox, MA

3. The Bookstore and Get Lit Wine Bar

The Bookstore and Get Lit Wine Bar

One of the best things to do in Lenox MA is to visit The Bookstore, a beloved establishment that has been a part of the community for over 40 years. This unique place offers a variety of experiences for locals and visitors alike. When it comes to books, The Bookstore has you covered. You’ll find a wide selection, ranging from modern-day fiction to poetry, including science fiction and Judaica. 

Additionally, they offer a great collection of children’s books, history, science, and even a New York cartoon compilation. What sets The Bookstore apart is its wine bar, conveniently located nearby. You can indulge in the pleasure of browsing through books while sipping on a glass of wine. It’s a tranquil and inviting spot, perfect for unwinding and engaging in intellectual discussions with fellow book enthusiasts, all while enjoying your chosen wine.

Address: 11 Housatonic St, Lenox, MA 01240, United States

4. Alta Restaurant & Wine Bar

Alta Restaurant Wine Bar

When it comes to the best things to do in Lenox MA, dining at Alta Restaurant & Wine Bar is a must. This exceptional restaurant is perfect for enjoying a delightful meal and excellent wine in the company of your loved ones. In 2008, Alta Restaurant & Wine Bar made its move to the elegant town of Lenox, and since then, it has become a beloved destination for both locals and visitors alike.

Founded by three dedicated restaurateurs, Alta Restaurant & Wine Bar is renowned for its creative Mediterranean cuisine and an impressive selection of delectable wines. Their commitment to using freshly sourced, local ingredients shines through in their lunch and dinner menus, which offer a delightful culinary experience for all patrons. Whether you’re seeking a casual lunch or a memorable evening dining experience, Alta Restaurant & Wine Bar is sure to exceed your expectations.

Address: 34 Church St, Lenox, MA 01240, United States

5. Berkshire Canoe Tours

Berkshire Canoe Tours

One of the most enjoyable activities for truly immersing yourself in a city is to embark on a captivating tour, and Berkshire Canoe Tours offers an exceptional experience. As a family-owned and operated business, they specialize in providing visitors with an entertaining and exhilarating adventure.

During the tour, you’ll have the opportunity to explore the breathtaking Housatonic River while taking in its stunning vistas and picturesque surroundings. Make sure to bring your camera or any recording device to capture those special moments that will serve as cherished memories. Along the way, you may encounter a variety of remarkable sights, including sycamores, cottonwoods, cinnamon ferns, owls, spice bushes, and much more.

Keep your eyes peeled during the two-hour tour, as it is common to spot fascinating wildlife such as muskrats, beavers, kingfishers, and great blue herons. Berkshire Canoe Tours offers an unforgettable experience that allows you to connect with nature and discover the wonders of the Housatonic River.

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6. Cranwell Spa And Golf Resort


When exploring the best things to do in Lenox MA, a must-visit destination is the Cranwell Spa And Golf Resort. Located near the vibrant Tanglewood live music scene, this stunning golf course promises an unforgettable experience for players of every skill level. Additionally, the resort boasts an indoor pool and a soothing sauna, providing a refreshing escape on hot days. 

As for dining options, the Cranwell Spa And Golf Resort restaurant offers a complimentary Continental breakfast, while the bar serves delightful beverages. Furthermore, fitness enthusiasts or those seeking to stay active can make use of the fitness center, conference center, and business spaces available on-site.

Address: 55 Lee Road Lenox, MA 01240, United States

7. Edith Wharton’s Home

Edith Whartons Home

If you’re a historian planning a vacation, a top recommendation on your list of enjoyable places to visit should undoubtedly be The Mount, Edith Wharton’s Home. With a rich history dating back to 1902 when Edith Wharton constructed the residence, The Mount stands as a captivating attraction. 

Situated on a vast 113-acre estate, this summer home of the renowned American novelist showcases impressive sculptures, exquisite architectural designs, expansive grounds, and a magnificent garden. Winter visitors are treated to a special annual light and sound event featuring breathtaking performances. Recognized as a National Historic Place, The Mount continues to serve as a cultural center celebrating the artistic, humanitarian, and intellectual accomplishments of Edith Wharton.

Address: 2 Plunkett St, Lenox, MA 01240, United States

8. Visit Lenox Library

Visit Lenox Library

When you’re in Lenox, one of the best things to do is visit the Lenox Library. If you have a passion for reading, this is an ideal place to explore. The library offers a delightful setting where you can discover captivating books, articles, audiovisual content, topical resources, and local history information. 

You can also delve into a wide range of music, join local clubs, and engage in outstanding lecture series. Additionally, the library hosts special events such as weddings, birthday parties, and corporate meetings. It’s a relaxing environment where you can immerse yourself in a fascinating book while admiring the beautiful architecture. 

You can also take a tour of the library and explore books that provide historical insights about Lenox. By doing so, you’ll gain knowledge about the town and its rich history. The library’s auditorium can accommodate up to 100 people, and the table seating capacity is 120 individuals. Plus, they offer free WiFi for internet access.

Address: 18 Main St, Lenox, MA 01240, United States

9. Hike to the Summit of Lenox Mountain

Summit of Lenox Mountain

When it comes to the best things to do in Lenox MA, exploring Lenox Mountain is a must, especially if you’re a history enthusiast. This prominent landmark holds a wealth of historical information and should be at the top of your visitation list. Lenox Mountain plays a significant role in the culture and history of the Mohican Nation, serving as their ancestral home and a vital part of their heritage even today. 

A trip to this attraction promises a rich learning experience. Standing at an impressive height of 2,126 feet, Lenox Mountain offers an ideal setting for hiking, running, and walking, boasting beautiful trails throughout the area. You can embark on a hike to reach the mountain’s summit and descend at your own pace. The panoramic views from the top are simply breathtaking and truly magnificent.

Address: Pleasant Valley Sanctuary

10. Ventfort Hall Mansion and Gilded Age Museum

Ventfort Hall Mansion and Gilded Age Museum

One of the best things to do in Lenox MA is to visit the Ventfort Hall Mansion and Gilded Age Museum. This iconic attraction is a must-see for anyone seeking a beautiful vacation in Lenox, and it should definitely be on your list of fun activities here. Constructed during the late 19th-century era of rapid economic growth, when wealthy individuals were building grand mansions, Ventfort Hall became the preferred residence for many affluent people in the region. 

With its impressive Jacobean architectural style, this mansion stood out as the finest venue for hosting extravagant parties in Lenox. Exploring the mansion, you’ll discover a range of fascinating features, such as an expansive veranda, intricately hand-carved oak ceilings, and meticulously maintained lawns, among many others. Throughout its history, Ventfort Hall has served various purposes, including a community center, a summer hotel, and even a hostel for students. 

In addition to touring the mansion, visitors can enjoy special exhibits, engaging programs, captivating theatrical plays, and enlightening lectures. Make sure to include a visit to Ventfort Hall Mansion and Gilded Age Museum when planning your itinerary of the best things to do in Lenox MA. It’s an experience that offers a glimpse into the opulent past and vibrant cultural scene of this charming town.

Address: 104 Walker St, Lenox, MA 01240, United States

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11. Theater at Shakespeare & Company Show

Theater at Shakespeare Company Show

If you have a passion for entertainment and the arts, visiting the Shakespeare & Company Show should be at the top of your list. This renowned show attracts more than 60,000 individuals every year and stands as one of the largest Shakespeare Festivals in the country. The company hosts a diverse range of events, showcasing both new plays and classic Shakespearean productions.

With its establishment dating back to 1978 by Tina Packer, Shakespeare & Company boasts a rich history and serves as a hub of entertainment for both locals and tourists alike. You’ll have the opportunity to enjoy beloved plays such as Hamlet, King Lear productions, Romeo and Juliet, and many more. 

Additionally, if you’re interested in learning about acting, the company offers workshops, lectures, and classes that you can actively participate in. For enthusiasts of theater and the works of William Shakespeare, immersing yourself in the Shakespeare & Company Show is an absolute must. Prepare to be captivated by the performances and embrace the vibrant atmosphere of this remarkable cultural institution.

Address: 70 Kemble St, Lenox, MA 01240, United States

12. WAM Theater

WAM Theater

One of the best things to do in Lenox, MA is to visit the WAM Theater, a significant cultural attraction with a strong focus on women’s history. The theater’s mission revolves around advocating for equal opportunities and human rights in society. If you have an interest in history, this is an ideal place to explore, as the artists here will provide detailed explanations of the diverse communities, races, nationalities, ethnicities, and backgrounds that have shaped the region.

You might be curious about the meaning behind the name “WAM,” which stands for “Where Arts and Activism Meet.” In 2010, the theater demonstrated its commitment to humanitarianism by making a monetary donation to support the fight for gender equality. Through its philanthropic efforts and dedication to social causes, WAM Theater has become a major draw for both the local community and visitors to the region.

Visiting the WAM Theater offers a unique opportunity to engage with the rich history and social activism associated with women’s rights. Immerse yourself in the powerful stories and artistic expressions that promote a more inclusive and equal society.

Address: 45 Walker St, Lenox, MA 01240, United States

13. Music Shows in Tanglewood

Music Shows in Tanglewood

When exploring Lenox, MA, one of the best things to do is visit Tanglewood. Renowned as the premier music center in the area, Tanglewood is home to the Boston Symphony Orchestra and hosts the highly acclaimed Tanglewood Music Festival. This region boasts a rich heritage, and since 1930, it has been graced with exceptional concerts featuring celebrated soloists, musicians, and conductors. 

Tanglewood has witnessed stellar performances by esteemed artists like Wind and Fire, Josh Groban, All-Star Band, Goo Goo Dolls, James Taylor, as well as the Chicago and Santana bands. To truly experience the magnificence of Tanglewood, a comprehensive tour of the entire area is highly recommended. Whether you’re planning a vacation in Lenox or seeking a memorable show, Tanglewood is an outstanding venue that should definitely top your list of things to do in Lenox MA.

Address: 297 West St, Lenox, MA 01240, United States

14. Explore Pleasant Valley Sanctuary

Explore Pleasant Valley Sanctuary

When in Lenox, a must-visit destination is the Pleasant Valley Sanctuary. If you’re an enthusiast of hiking amidst breathtaking landscapes, this is the perfect place to be, and it should definitely be at the top of your list of enjoyable locations to explore. Spanning over 1,000 acres, this sanctuary offers visitors a wealth of adventure. 

Numerous trails wind through the stunning forests, wetlands, meadows, and along the slopes of Lenox Mountain. Additionally, the sanctuary organizes various events and programs for visitors to partake in. These include opportunities for canoeing or paddling, guided hikes led by naturalists, kayaking excursions, bird watching programs, and much more. 

Keep an eye out for the beavers that inhabit the sanctuary—they can often be spotted near the many dams in the area, which are truly worth seeing. Don’t forget to bring your camera to capture some incredible photos to share on your Instagram feed.

Address: 472 W Mountain Rd, Lenox, MA 01240, United States

15. Kennedy Park

Kennedy Park

Discover the best things to do in Lenox MA by exploring Kennedy Park, an incredible destination that offers a plethora of enjoyable outdoor activities. Immerse yourself in a world of excitement and add this park to your must-visit list. With approximately 15 miles of well-kept trails, it’s an ideal location for hiking and biking enthusiasts. 

Moreover, it provides a picturesque setting for delightful picnics with colleagues, family, and friends, offering stunning views to enhance your experience. Bring the little ones along as well, as there are dedicated trails and play areas for them to enjoy. For a truly breathtaking experience, plan your visit during the autumn season to witness the vibrant fall foliage in all its glory. 

From mountain biking and cross-country skiing to snowshoeing and hiking, Kennedy Park caters to a wide range of interests. Please note that automobiles, snowmobiles, and electric bicycles are not permitted, ensuring a peaceful atmosphere. Rest assured, there are ample parking spaces available for your convenience.

Address: Route 7 and 20 Pittsfield Road, Lenox, MA

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Frequently Asked Questions

What are the best things to do in Lenox MA?

Lenox MA offers a range of exciting activities. Immerse yourself in serene green spaces, enjoy live music at the renowned Tanglewood Music Festival, and explore the town’s fascinating history through its libraries and museums.

What makes Lenox MA a great destination?

Lenox MA is a charming town known for its serene atmosphere, picturesque green spaces, and cultural offerings. Whether you seek tranquility in nature or enjoy live music performances, Lenox has something for everyone.

What outdoor activities can I enjoy in Lenox MA?

Lenox MA is a haven for outdoor enthusiasts. You can explore majestic parks, hike scenic trails, and even enjoy concerts amidst nature. The town offers abundant opportunities for outdoor fun and relaxation.

What is the Tanglewood Music Festival?

The Tanglewood Music Festival is a world-renowned event held in Lenox MA. It showcases exceptional performances by renowned musicians and orchestras. Attending the festival is a must-do for music lovers visiting Lenox.

Are there historical attractions to explore in Lenox MA?

Absolutely! Lenox MA boasts a rich history. You can explore its libraries and museums to delve into the town’s past. Discover fascinating stories and artifacts that offer insights into Lenox’s cultural heritage.

Is Lenox MA a family-friendly destination?

Yes, Lenox MA is perfect for family vacations. The town offers a peaceful atmosphere, beautiful green spaces for children to play, and cultural events that cater to all age groups. There are plenty of activities to keep everyone entertained.

Can I experience both nature and culture in Lenox MA?

Certainly! Lenox MA seamlessly combines natural beauty and cultural experiences. You can immerse yourself in the tranquility of green spaces while also enjoying live music performances and exploring the town’s cultural offerings.

What can I expect from a trip to Lenox MA?

A trip to Lenox MA promises an unforgettable experience. You can expect to be surrounded by scenic landscapes, attend world-class music performances, delve into history, and create cherished memories with your loved ones.

When is the best time to visit Lenox MA?

Lenox MA is beautiful year-round, but the summer months offer the best weather for outdoor activities and attending events like the Tanglewood Music Festival. However, each season has its own charm, so it ultimately depends on your preferences.

Are there accommodations available in Lenox MA?

Yes, Lenox MA offers a variety of accommodations to suit different budgets and preferences. You can find charming bed and breakfasts, cozy inns, and even luxury resorts in and around the town.

Can I visit Lenox MA for a day trip?

Absolutely! Lenox MA is a great destination for day trips. You can explore the town’s attractions, enjoy outdoor activities, and even catch a concert at Tanglewood, all within a day. However, if time permits, consider staying longer to fully experience what Lenox has to offer.

Are there dining options in Lenox MA?

Lenox MA has a diverse culinary scene. You’ll find a range of restaurants, cafes, and eateries offering various cuisines, including local New England favorites. From fine dining to casual bites, there’s something to satisfy every palate.

Can I enjoy shopping in Lenox MA?

Yes, Lenox MA offers delightful shopping experiences. The town has unique boutiques, art galleries, and specialty stores where you can find one-of-a-kind items, souvenirs, and locally crafted goods.

Are there any festivals or events in Lenox MA?

Lenox MA is known for its vibrant events calendar. Besides the famous Tanglewood Music Festival, you can enjoy art festivals, seasonal celebrations, and cultural events throughout the year. Check the town’s event listings to see what’s happening during your visit.

Is Lenox MA accessible for people with disabilities?

Lenox MA strives to provide accessibility for all visitors. Many attractions, accommodations, and facilities have wheelchair ramps and accessible features. It’s always a good idea to contact specific places in advance to ensure they can accommodate your needs.

Can I explore the surrounding areas of Lenox MA?

Yes, Lenox MA serves as a gateway to the beautiful Berkshire region. You can explore neighboring towns, visit museums and galleries, hike in scenic landscapes, and discover even more cultural and natural attractions beyond Lenox.

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Final Thoughts

When it comes to the best things to do in Lenox MA, this charming town offers an enchanting blend of natural beauty, cultural experiences, and historical wonders. From the tranquil green spaces to the captivating music festivals, Lenox invites you to embark on an unforgettable journey. 

So pack your bags, immerse yourself in the serenity of this picturesque destination, and create cherished memories that will last a lifetime. Lenox is waiting to delight you with its myriad of delights, making it the ultimate getaway for those seeking a truly remarkable experience.


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