Lenox

Day Trips

Make the most of your day with our curated plans, packed with Lenox's hidden gems and unique experiences!

day 1
Nature Walks and Scenic Views
morning
:

Start your day with a refreshing walk at Kennedy Park, surrounded by beautiful trees and trails. Enjoy the fresh air and peaceful sounds of nature as you explore the park's various paths.

afternoon
:

Head to the Lenox Village to grab lunch at a local café. Afterward, visit the Berkshire Museum for a glimpse into regional art and history.

evening
:

Relax for dinner at one of Lenox's charming restaurants. Catch a local theater performance to end your day on a cultural note.

day 2
Cultural Discoveries
morning
:

Visit Tanglewood to explore the beautiful grounds before attending a concert. Take advantage of early morning tours that showcase the historical significance of the place.

afternoon
:

Stop by the Norman Rockwell Museum to appreciate American art. Have a leisurely lunch at a nearby bistro as you discuss your favorite exhibits.

evening
:

Join a guided sunset hike at a nearby trail for stunning views. Wind down with some stargazing if weather permits.

day 3
Autumn Adventures
morning
:

Take a guided tour of the picturesque gardens at the Ventfort Hall Mansion. Experience the rich history and details of this longstanding estate.

afternoon
:

Enjoy a scenic drive through the fall foliage in the surrounding Berkshires. Stop for lunch at a farm-to-table restaurant showcasing local ingredients.

evening
:

Visit a local winery for a relaxing evening of wine tasting. Dine at a cozy spot that specializes in seasonal dishes.

day 4
Artistic Inspirations
morning
:

Start with a visit to the Chesterwood Museum, a former studio of sculptor Daniel Chester French. Stroll through the gardens and enjoy the beautiful landscape.

afternoon
:

Attend a painting workshop at a local art studio, where you can unleash your creativity. Enjoy lunch at a café nearby that features local artists' work.

evening
:

Head to a gallery opening or art show in Lenox for some evening inspiration. Have dinner at a restaurant known for its artistic presentation of food.

day 5
Relaxing Retreat
morning
:

Spend a leisurely morning at a local spa indulging in rejuvenating treatments. Enjoy a healthy breakfast at the spa or a nearby café afterward.

afternoon
:

Explore the quaint shops in downtown Lenox for unique souvenirs. Take your lunch at a charming delicatessen known for its homemade offerings.

evening
:

Join a yoga class for some mindfulness and relaxation. End the day with a tranquil dinner at a restaurant featuring a garden view.

day 6
Outdoor Thrills
morning
:

Embrace an adventurous day by going mountain biking at one of the local trails. Keep your energy up with a hearty breakfast at a local diner.

afternoon
:

Pack a picnic and head to the nearby Stockbridge Bowl for an afternoon by the water. Kayak or paddleboard to enjoy the scenery.

evening
:

Return to Lenox for dinner at a restaurant with a welcoming atmosphere. Catch a live music event to complete your outdoor day.

day 7
Culinary Delights
morning
:

Start your culinary journey at a local farmer's market to gather fresh ingredients. Enjoy a cooking class where you can prepare a traditional Berkshires dish.

afternoon
:

Savor your homemade meal for lunch and explore the culinary history of Lenox. Visit nearby farms to learn about local produce and specialties.

evening
:

Reflect on the day over dinner at a farm-to-table restaurant. Consider a dessert tasting at a local bakery to satisfy your sweet tooth.

day 8
Wellness Retreat
morning
:

Begin your day with a sunrise meditation session in a serene outdoor space. Follow this with a wholesome breakfast at a health-focused café.

afternoon
:

Join a guided hike to practice mindfulness in nature. Enjoy a nutritious lunch packed with local ingredients.

evening
:

Attend a wellness workshop or talk featuring local health experts. Wind down your day with herbal tea in a relaxing setting.

day 9
Music and Arts
morning
:

Visit the Boston Symphony Orchestra at Tanglewood for a morning rehearsal or concert. Enjoy the ambiance of the surrounding nature.

afternoon
:

Head back to Lenox for lunch at a café with a music theme. Explore local shops offering musical instruments and art supplies.

evening
:

Attend a concert at one of the local venues for an entertaining evening. Relish a late dinner with live music accompanying your meal.

day 10
Camping and Bonfires
morning
:

Set out early to a nearby campground for a fun-filled outdoor adventure. Enjoy breakfast by the campfire with fresh coffee and pastries.

afternoon
:

Engage in activities like hiking and fishing with family or friends. Gather for a packed lunch amidst nature to recharge.

evening
:

As sunset approaches, prepare for a classic campfire with s'mores. Share stories and enjoy a night under the stars.

Discover Lenox

Read more in our Lenox 2024 Travel Guide.

Lenox Travel Guide