From the New York Area: Litchfield, CTWhat's There: Litchfield is a base for exploring the surrounding Litchfield Hills, a region of classic New England beauty, with winding roads, charming villages and covered bridges. It's at its best in October, with fall foliage at its peak.
Getting There: Litchfield is a little more than two hours from New York; allow $24 - $64 for gas, including some driving around the Litchfield area.
Where to Sleep and Eat: The Abel Darling Bed & Breakfast, located in downtown Litchfield, has four lovely rooms that run from $120 - $190 a night. For lunch, Wood's Pit BBQ & Mexican Cafe, near Bantam Lake, offers down-home barbecue favorites in an unpretentious atmosphere (look for the lunch specials -- under $15). In between antique shops in Woodbury, grab some gourmet goodies at natural and organic New Morning (under $10). For dinner, enjoy inventive American cuisine at the Village Restaurant (about $50). The next night, try the sophisticated fare at the cozy West Street Grill, also in Litchfield (about $60).
What to Do: Haight-Brown Vineyard in Litchfield offers tastings from $8.50 (including a signature glass). Wander the retail store and display gardens of White Flower Farm, a great place to get ideas for your own plot of land at home. The $5 admission fee to the Litchfield History Museum allows you to see not only the museum's collections (furniture, paintings and other historic objects) but also the Tapping Reeve House & Law School, where you can catch a glimpse of what school was like for a 19th-century student. Don't miss a quick stop at Litchfield's photogenic Congregational Church (free). Litchfield has many boutiques and quirky shops for browsing, but serious antique lovers should head to Woodbury, a small town about half an hour away that has been called the antiques capital of Connecticut. Outdoorsy types can visit the White Memorial Conservation Center in Litchfield, which offers a nature museum (admission $6) as well as boating, picnicking, hiking, biking and cross-country skiing opportunities.
The Bottom Line: Transportation, two nights' hotel, two lunches and two dinners total $267 - $357 per person, with plenty to spare for sightseeing.
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--written by Sarah Schlichter; updated by Christina Livadiotis