Plan the Perfect Berkshires Weekend
Looking for inspiration for your next escape to the mountains? Whether you're craving outdoor adventure, cultural experiences, or just a peaceful retreat, the Yankee Inn is the ideal home base for your Berkshires getaway. We've crafted a selection of weekend itineraries to help you make the most of your stay — from scenic hikes and farm-to-table dining to world-class music and cozy nights by the fire. Browse our sample plans, tailor them to your interests, and get ready to relax, explore, and recharge in beautiful Lenox, MA.
SUMMER / FALL
FRIDAY
Arrival & Relaxation
3:00 PM – Check-in at the Yankee Inn
Settle into your comfortable room — maybe one with a private balcony — and enjoy views of the Berkshire hills.
5:00 PM – Dinner in Lenox Village
Head into downtown Lenox (just a 5-minute drive) for dinner at Brava Wine Bar. Cozy and distinctly Berkshires.
7:30 PM – Nightcap & Stargazing
Return to the Yankee Inn for a glass of wine in our lounge or relax in the indoor heated pool. On a clear night, the skies are perfect for stargazing from your balcony or patio.
SATURDAY
Explore Nature & Culture
8:00 AM – Complimentary
Hot Breakfast at the Inn
Fuel up with eggs, pastries, coffee, and more before a full day of adventure.
9:00 AM – Hike at Pleasant Valley Wildlife Sanctuary (5 minutes away)
Enjoy scenic trails through forests, wetlands, and up to Lenox Mountain Summit for stunning views of the valley.
12:00 PM – Lunch in Downtown Lenox
Try The Olde Heritage Tavern for a casual bite. Stop by Berkshire Cone truck for some locally homemade ice cream or gelato.
1:30 PM – Afternoon at The Mount
(Edith Wharton's Estate)
Tour the Gilded Age mansion and gardens, stroll through the forested grounds, or take a guided literary or ghost tour (seasonal).
4:00 PM – Relax at the Inn
Take a dip in the pool, enjoy a cup of tea, or freshen up before your evening plans.
6:30 PM – Dinner & Performance at Shakespeare & Company or Tanglewood (Seasonal)
Enjoy fine dining at Gateways Inn followed by a world-class theatrical or musical performance — both venues are within 10 minutes of The Yankee.
SUNDAY
Wind Down in Wellness
8:30 AM – Breakfast at the Inn
10:00 AM – Stroll Kennedy Park Trails
Just down the road, these peaceful wooded trails are great for a gentle walk or light jog before checkout.
12:00 PM – Check-out
(and maybe a spa stop!)
Say goodbye to the Yankee Inn — or stop at Canyon Ranch Spa, Miraval or Kripalu Center for a massage or yoga session before heading home.
FRIDAY
Arrival & Fireside Comfort
3:00 PM – Check-in at the Yankee Inn
Warm up in your cozy room, many featuring gas fireplaces, plush bedding, and views of snow-covered pines.
5:00 PM – Dinner in Lenox Village
Head to Cello or Alta Restaurant & Wine Bar for a farm-to-table meal in a charming, candle-lit atmosphere.
7:00 PM – Hot Cocoa & Indoor Pool Time
Return to the Yankee Inn to enjoy a relaxing swim in the indoor heated pool, followed by hot cocoa in the lounge or snuggled up in bed by the fire.
SATURDAY
Snow Adventures & Local Flavor
8:00 AM – Complimentary Hot Breakfast at the Inn
Start your day with a hearty breakfast featuring eggs, waffles, and fresh coffee — perfect fuel for a winter day.
9:30 AM – Ski or Snowboard at Bousquet Mountain (10 minutes away)
Spend the morning on the slopes with skiing, snowboarding, or tubing at this family-friendly ski area.
1:00 PM – Lunch at Antimony
Warm up with seasonal soups, sandwiches, and local craft beer just a short drive from the mountain.
2:00 PM – Afternoon at the Norman Rockwell Museum (weather-friendly indoor activity)
Immerse yourself in world-renowned art and history while staying warm and inspired.
4:00 PM – Après-Ski Back at the Inn
Unwind in your room with a warm bath, a book by the fireplace, or a nap before dinner.
6:00 PM – Dinner & Drinks at Firefly Gastropub
Enjoy a cozy, relaxed meal with craft cocktails and a creative menu — just a few minutes from the Inn.
SUNDAY
Slow Morning & Scenic Send-Off
8:30 AM – Breakfast at the Inn
10:00 AM – Winter Walk at Kennedy Park or Pleasant Valley Sanctuary (weather permitting)
Take a short, peaceful walk through snowy woods and spot winter birds and animal tracks. Snowshoe rentals available at the Arcadian Shop
12:00 PM – Check-out & Optional Spa Stop
Wrap up your winter retreat with a visit to Canyon Ranch or Kripalu Center for a massage, yoga class, or sauna session before heading home.
WINTER
SPRING
FRIDAY
Arrival & a Taste of Lenox
3:00 PM – Check-in at the Yankee Inn
Settle into your bright and spacious room. Enjoy the fresh spring air from your private balcony or unwind by the gas fireplace if there’s still a chill in the air.
5:30 PM – Dinner in Lenox Village
Start the weekend with a cozy dinner at Alta Restaurant & Wine Bar or Ombra, both offering seasonal menus with locally sourced ingredients.
7:00 PM – Relax by the Fire or Take a Sunset Stroll
After dinner, take a quiet walk along the property or sip wine by the fireplace as the sun sets behind the Berkshire hills.
SATURDAY
Nature, History & Art
8:00 AM – Complimentary Hot Breakfast at the Inn
Wake up to a full hot breakfast with fresh coffee, pastries, eggs, and more.
9:30 AM – Morning Hike at Kennedy Park or Olivia’s Overlook
Take in the beauty of early spring with a scenic hike. Trails are lined with budding trees, and the crisp mountain air is invigorating.
12:00 PM – Lunch in Stockbridge
Head to Once Upon a Table (weekends only) a charming café tucked off of Main Street for a light and locally inspired lunch.
1:30 PM – Afternoon at The Mount (Edith Wharton’s Estate)
Wander the elegant grounds and tour the historic mansion as spring blooms return to the gardens. Guided tours resume in spring, weather permitting.
4:00 PM – Relaxation Time at the Inn
Unwind with a dip in the indoor heated pool or enjoy a book on your balcony as the breeze rolls in.
6:30 PM – Dinner & Live Music
Try Firefly Gastropub for an energetic evening out. On weekends, you’ll often find live music or local events in town.
SUNDAY
Garden Walks & Goodbye
8:30 AM – Breakfast at the Inn
10:00 AM – Visit Berkshire Botanical Garden (Open April–October)
Just 15 minutes away, this 15-acre garden explodes with color in the spring and offers a relaxing, beautiful way to end your weekend.
12:00 PM – Check-out & Optional Stop in Great Barrington
On your way home, explore Great Barrington’s boutiques, cafes, and bookstores for a final taste of the Berkshires.