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A Winter Weekend
The
Berkshires
Mountains, art, and a little bit of magic
for Abby
February 14 – 16, 2026
♥
Our Weekend Itinerary
Saturday
February 14
Valentine's Day
Morning
Leave Boston
Head west — the Berkshires are calling.
Late AM
Yankee Candle Village
South Deerfield. A warm, fragrant first stop. Lunch at the brewery in the back.
Afternoon
The Mohawk Trail
One of the most beautiful drives in Massachusetts. Stop at the Hairpin Turn for the overlook.
3–4 PM
Check in — The Trail in Adams
Artist-decorated boutique inn at the foot of Mount Greylock. Organic everything. Settle in.
Evening
Aperitivo at the Distillery
Forager Gin & Ski Bum Rum at Greylock WORKS. Craft cocktails in a beautifully restored mill.
8 PM
Dinner at STATE Food + Drink
Vietnamese-American & California roots. Seasonal, locally sourced. Also at Greylock WORKS.
Sunday
February 15
art & trails
Morning
Breakfast at the Inn
Organic breakfast with fresh fruits, baked goods, and good coffee. No rush.
10 AM
MASS MoCA
One of the world's largest contemporary art museums. Open 10–5. Give it at least two or three hours. Multiple lunch options
Afternoon
The Cascades Trail
A short walk to a waterfall in North Adams. Bring sturdy boots — it may be icy.
Dinner
Hancock, MA - almost NY state!
Bluebird & Co.
Monday
February 16
Presidents' Day
Morning
Breakfast & Check Out
One last organic breakfast. Say goodbye to Adams.
9 AM
Cross-Country Skiing at Notchview
3,000 acres of groomed Nordic trails in Windsor, 30 min from Adams. Ski rentals on site — arrive early on the holiday weekend.
Afternoon
Drive Home to Boston
Warm, tired, and happy.