Chatham Bars Inn
297 Shore Road, 508-945-0096, www.chathambarsinn.com. Nightly rates in June $329-$1,825. Spa treatments range from $25-$440 for package deals; appointments can be made by calling 508-945-6737. Stars, the fine-dining establishment, serves breakfast and dinner; try the Sacred Cod, the more relaxed tavern, for a light lunch. The inn is a 10-minute walk to downtown, where Main Street is dotted with cute boutiques, antiques shops, and restaurants ( Impudent Oyster has excellent seafood).
637 Main St., 508-945-4900, www.chathamorpheum.org
Chatham’s one and only cinema when it opened in 1916, the Orpheum shut its doors in 1987. It was resurrected last year as a nonprofit theater. It’s a charming spot with a nice mix of mainstream and art-house options, not to mention the classics (“Breakfast at Tiffany’s” recently screened). VERS, its lobby cafe, serves light and delicious bistro fare (soups, salads, sandwiches) and an assortment of drinks (beer, wine, coffee, juices), all of which you can take inside the theater.
The Chatham Squire
487 Main St., 508-945-0945, www.thesquire.com
Belly up to the bar and have a pint with the locals at this watering hole that gets a good cross section of the neighborhood, from older couples sipping wine to college bros rolling up their sleeves to compare Bruins tattoos. This is where most folks in town end up for nightly entertainment, with live music, DJs, and karaoke on the bill.
Chatham Candy Manor
484 Main St., 508-945-0825, www.candymanor.com
Calling all sweet-tooth fanatics: Behold your Cape Cod mecca. This beloved candy shop dates to 1955 and brims with all sorts of things that’ll get you in trouble: fudge, truffles, various nut clusters, turtles, and caramels. Sold by friendly women prone to call you “hun,” the goodies come in cute little boxes. It’s no wonder the website brags, “If they weren’t made of chocolate, they’d be signed by the artist.”