Rockport is north of Gloucester along Route 127 or 127A. At the end of Route 128, turn left at the signs for Rockport to take Route 127, which is shorter but more commercial. To take Route 127A, which runs near the east coast of Cape Ann, continue on Route 128 until you see the sign for East Gloucester and turn left. Parking is tough, especially on summer Saturday afternoons, but metered spots are available throughout downtown. Make one loop around downtown and then head to the free parking lot on Upper Main Street (Rte. 127). The shuttle bus to or from downtown costs $1.
The commuter rail (tel. 617/222-3200; www.mbta.com) runs from Boston's North Station. The trip takes 60 to 70 minutes, and the round-trip fare is $16. The station is about 6 blocks from the downtown waterfront. The Cape Ann Transportation Authority, or CATA (tel. 978/283-7916; www.canntran.com), runs buses from town to town on Cape Ann Monday through Saturday.
The Rockport Chamber of Commerce, 170 Main St. (tel. 978/546-6575; www.rockportusa.com), is a division of the Cape Ann Chamber of Commerce (tel. 978/283-1601; www.capeannvacations.com). The chamber operates an information booth on Upper Main Street (Rte. 127) daily from July 1 through Labor Day and on weekends from mid-May to June and early September through mid-October. It's about a mile from the town line and a mile from downtown -- look for the WELCOME TO ROCKPORT sign on the right as you head north. Ask for the pamphlet Rockport: A Walking Guide, which contains a good map and descriptions of three short walking tours.
Rockport Music organizes the Rockport Chamber Music Festival (tel. 978/546-7391; www.rcmf.org), which takes place each June. It's a good excuse to see the town before the height of tourist season. In addition to performances by promising young musicians and family-oriented concerts (tickets $20-$35), events include free lectures and discussions. Performances take place in the lovely Shalin Liu Performance Center, 37 Main St., which opened in 2010 to great acclaim. Check ahead for the schedule of events in the 330-seat concert hall, noted for the 2-story window overlooking the water at the back of the stage.
The annual Christmas pageant, on Main Street in December, is a crowded, kid-friendly event with carol singing and live animals.