Starting Point: PORTLAND Drop by the Portland Museum of Art, to see pieces by Degas, Cassatt, and Renoir. Drive north through the picturesque Sebago Lake Region of Maine to NORTH CONWAY, NH, where you can take a ride on the Conway Scenic Railroad. Head south a few miles to the Darby Field Inn & Restaurant, a charming B&B where the staff can arrange a romantic carriage ride along forest trails.
The next day, take the Kancamagus Highway over the mountains for primo leaf peeping. (For foliage conditions, call 800-258-3608.) For a dose of roadside kitsch, head west to Lincoln, and visit Clark's Trading Post, to take in the live bear show. Take New England Interstate Rte. 10 S to HANOVER. Detour down NH 120 S to Lebanon, and Poverty Lane Orchards, where you can pick your own apples or buy local treats at the farm stand.
From Lebanon, take US-4 to WOODSTOCK, VT, and head to Bentley's for burgers and regional microbrews. When you reach VT Rte. 100A, head south to PLYMOUTH, and one of the most beautiful historic sites in New England: the President Calvin Coolidge State Historic Site (802-672-3773). Head south, then southwest, on US-9 to BENNINGTON. Spend the night at the Four Chimneys Inn, a classic, 11-room inn, whose restaurant was frequented by guests such as Elizabeth Taylor and Walt Disney in the 1950s. For a Revolutionary War fix, visit the Bennington Battle Monument (802-447- 0550). An elevator will take you to an observation room near the top of the tower for spectacular views. Also check out the covered bridges of Bennington County; and the Bennington Museum, which houses the largest public collection of paintings by Anna Mary Robertson "Grandma" Moses.
From Bennington, take US-7 toward the Berkshires, and WILLIAMSTOWN, MA. There, make a stop at the Sterling and Francine Clark Art Institute, and the Williams College Museum of Art. If you'd like to stay in the area for the night, we suggest The Guest House at Field Farm, featuring contemporary design, as well as landscaped sculpture gardens.
South of Williamstown is the small town of LENOX. It was a Gilded Age resort mecca during the "Berkshire Cottage Era" (1880-1920), a time made famous by author Edith Wharton, who lived for many years at The Mount Estate and Gardens. Today, you can tour the estate, and enjoy a glass of wine at the Terrace Café. Continuing south, you'll reach STOCKBRIDGE, where Norman Rockwell lived and worked in the final decades of his career. Visit the Norman Rockwell Museum to see the largest collection of his works. Also in the area: the Chesterwood Estate & Museum, the summer home of sculptor Daniel Chester French (his works include the statue of a seated Abraham Lincoln at the Lincoln Memorial in Washington, D.C.). Check into the historic Red Lion Inn, which has been continuously operating since the 18th century. As you head south toward Connecticut, look out for the dozens of antiques shops as you pass through SHEFFIELD and the rest of Litchfield County.
Take US-44 to SALISBURY, CT, a picture-perfect little hamlet. Wander the shops and stop at the Roast Coffeehouse (860-435-0600) for a cup of joe and a freshly baked pastry. Back on US-7, you'll come across a barn-red covered bridge, which is the gateway into WEST CORNWALL, home to Clarke Outdoors. Rent a canoe and take a 10-mile jaunt on the Housatonic River. About 7 miles south is Kent Falls State Park, a lovely place to take a break. Hike around an impressive waterfall and surrounding woods. From KENT, keep following US-7 about 13 miles, then turn left on US-202 and follow that into__NEW MILFORD__. Stop for lunch at Adrienne Fine American Dining, for delicious American cuisine served in a cozy 18th-century home. Back on US-7, continue south to NORWALK, then head for the South Norwalk (or SoNo) district, to find a cluster of shops, bars, and restaurants—stop for a cup of coffee at SoNo Caffeine (203-857-4224). Spend the night in GREENWICH, where dinner and a room await at the Homestead Inn, only about an hour away from New York City's airports.