RELATED LINKS Return to 5 Beautiful Drives

Natural beauty and literary luminaries share the spotlight in Pittsfield, Mass., gateway to the Berkshires and former residence of celebrated writers such as Nathaniel Hawthorne, William Bryant and Oliver Wendell Holmes. It was at the city's Arrowhead estate (www.mobydick.org) where Herman Melville wrote Moby Dick, allegedly inspired by the whale-like proportions of looming Mount Greylock to the north. Today, the property is home to the Berkshire County Historical Society (www.berkshirehistory.org), where you can leaf through the history of western Massachusetts' Pioneer Valley.

Flanked by brilliantly colored beech, maple, pine, birch and hemlock trees, State Route 9 heads east through the rural community of Cummington. Here, the Kingman Tavern Historical Museum (www.virtual-valley.com/kingman) offers a glimpse inside an early 1800s tavern, 1840s cider mill and turn-of-the-century barn, carriage shed and country store. Pass Goshen's picturesque row of book dealers, bakeries and crafts shops and take a snack break at the Williamsburg General Store (www.wgstore.com), where the fragrance of spices and candles mingle with the scent of freshly baked bread, maple syrup and honey.

Continue east to Graves Farm Wildlife Sanctuary (www.massaudubon.org). Its easy, mile-long trail loops through a forest of pine, oak and beech trees, where jewel-toned leaves crunch underfoot and birds and beavers make their home. Early October is the peak time for fall color in this area.

Observe an entirely different sort of wildlife in Northampton and Amherst, where 30,000 students are enrolled in the area's five schools: University of Massachusetts-Amherst and Hampshire, Smith, Mount Holyoke and Amherst colleges. The 8.5-mile Norwottock Rail Trail, an 1887 railroad now used by hikers, joggers and bicyclists, connects the two coed-crawling towns. Nearby Cowls Sawmill (www.cowls.com) offers agritourism with its classic New England timber processing tour.

From Amherst, follow scenic Route 116 along the east bank of the Connecticut River to South Deerfield, where breathtaking views of the nearby Holyoke Mountains are rivaled only by the 90,000 square foot Yankee Candle Company compound (www.yankeecandle.com). Although it's usually teeming with shoppers, the factory is worth a visit for its antique candle making museum and dip-your-own candle room.

Continue north through the Connecticut River Valley's fertile farmland to the Old Deerfield National Historic Landmark (www.historicdeerfield.org), an interactive museum village on 1,000-acres, showcasing the region's role in early American history, arts and culture. From there, head back east along Route 2. Locally known as "The Mohawk Trail," this pre-Colonial Indian footpath is one of the state's most popular foliage routes.

Along the way, photo ops include the Bridge of Flowers, an unused bridge spanning Deerfield River draped in a dazzling display of flora. A short distance downstream, more than 50 dramatic rock cavities at Glacial Potholes are the result of granite-grinding Ice Age erosion. In Shelburne Falls (www.shelburnefalls.com), take a ride on a restored 1896 trolley at the Trolley Museum (www.sftm.org), then stroll along Bridge Street, the town's main drag lined with antique shops. Free two-hour parking is available throughout the area.