36(ish) hours in the Berkshires

Friday:7:30 PM: Head to Route 7 Grill (999 Main St., Great Barrington, MA) for some of the best farm-to-table BBQ around. Eat pulled pork, baked beans, corn bread, and some that amazing macaroni and cheese with the hardened cheesey top. Buy an "eat meat" shirt on the way out.

9:00 PM: Drive to up route 7 into Dalton. Eat the raspberry filled sugar cookie that your mom has brought to the house. Sleep like you're dead.

Saturday:

12:00 PM: Drive to Lenox. Poke around The Bookshop, grab an ice cream cone at SoCo Creamery, and walk through the craft fair across the street from the library.
6:00 PM: Visit Tanglewood for the last concerts of the season at the Jazz Festival. Put your quilt down and fire-up your tea lights. Climb the tree and wander around in the maze before it gets too dark. Have a glass of wine, eat some olives, talk about teaching and college and golf with your parents.

8:00 PM: Eat Peter's summer chili with homemade fresh salsa. Put your fleece on (it's already chilly), and lie back to watch for shooting stars.
Sunday:
12:30 PM: Head to Saratoga for the last horse races of the season. Read what the experts are picking and place $2 bets on the long-shots for every race. Win big.

5:00 PM: Walk around Saratoga. Wander into the wine store if they're doing a tasting, buy a scarf, check the sale rack at the Gap.

7:30 PM: Eat dinner at Max London's (466 Broadway, Saratoga Springs, NY). Order the lemony anchovie crostini and the fantastic clam pizza.

8:30 PM: Stop at Eugenio's Cafe (419 Broadway, Saratoga Springs, NY) for a bambini gelato and a quick coffee before the drive home. Good bye summer, hello New York.

Update on 10/12/12: Fun news, friends! I put together a mini travel guide on the Berkshires. I kept it short so that I was only sharing my absolute favorite things in that area. Hope you enjoy!