During the Fall 2008 semester, Simon's Rock is running a free shuttle to/from the Day's Inn. Read: free ride up/down the hill. On your way back up, look for it in the middle of the Day's Inn parking lot.
Bill’s Pharmacy: It’s a little store on the corner of Taconic and Main. When Health Services prescribes you drugs, that’s where they go to pick them up. You can also buy tickets for the Peter Pan Bus here, but it's cash only. This is one way to get to NYC, Boston, or elsewhere.
Visitor’s Center: Little hut outside Bill’s; they can give you half-price tickets to events around the Berkshires. The bus stops outside of the Center.
Mahaiwe Theatre: On Castle Street this theatre just reopened recently and is really pretty. Various people use it (i.e. Barrington Stage Co. or the Berkshire Opera) but it is also a venue for people touring or something.
Threads: Across the street from Cumberland Farms, but back towards the center of town a little bit. A vintage store with cool moderately-priced clothing. At least one badass jacket has been bought there. They also have hair dyes and bleach.
The Vault Gallery: Owned by a crazy lady named Marilyn, usually pretty good art.
The Coffee Shop/Fuel: A great little coffee shop. They do all the normal espresso drinks, teas, and pastries, plus crepes (sweet and savory) and smoothies. "The Classic" smoothie is highly recommended. Also a nice place to hang out. Free wi-fi. [Password is 4135285505]
Tom’s Toys: Toy store that has mad dinosaur paraphernalia and other good toys.
The Gifted Child: Another toy store, they sell really small plastic babies. They are really nice, but Tom’s Toys has better toys according to some. Check it out, though.
The Chef's Shop: Lots of cookery, not very expensive.
Crystal Essence: Hippie store with nice clerks and weird jewelry. Also a lot of New-Age-y books.
The Triplex: Movie theatre that shows a mix of indie/local films and big Hollywood pictures, usually three at one time.
The Garden: A skate shop that has a really cool owner and neat clothes. Located on Railroad Street above Lily's (some weird fashion store).
Tune Street: Record store that focuses more on tourists, large televisions, and stereo equipment than music. Decent selection, sort of.
Barrington Outfitters: Store with clothes and shoes. Prices that cater to tourists, but they have some good things.
Expeditions: An outdoor store with moderate prices. They rent kayaks and stuff. Extreme. Expeditions has now shut down but might open up soon at Butternut Ski Resort.
Carr Hardware: A large hardware store…nothing out of the ordinary. Awesome, though, if you're into that sort of thing.
Yellow House Books: A used book store with neat books and a sweet lady that runs it.
Rite Aid: Another drug store; there’s a B-Bus stop outside of it.
Cumby’s: A gas station that is open 24 hours. They have 69 cent slushies. And gummi dinosaurs. Can you actually ask for more than that? Making "Cumby's runs" in the wee hours of the morning is something of a common pasttime, mainly since in addition to selling cigarettes they also sell food (snacks, bread, donuts, microwavable pizzas, and so on) and are the only place open that sells food in the whole town after the Snack Bar closes (if you don't count vending machines).
Getty: A full service gas station. They, along with Cumby’s, have the cheapest gas in town. They are one of the few vendors of Nat Shermans in Great Barrington. The other vendors are Gorham & Norton deli and package store, and Domaney's liquor store.
The Music Shop: A music shop. Currently out past Price Chopper, but on Railroad Avenue starting October 08. Run by Sean and Claudia, who live down the road from campus and drive eighty year old cars.