Brattleboro is a city of 12,000 people in southern Vermont. From points south, it will most likely be the place for travelers to begin their exploration of Vermont.
- Route 9. Runs East-West through town. Going west it hits Bennington, and to the east, Keene.
- Greyhound, terminal at 1102 Putney Rd, near exit 3 on route 91.
- Amtrak, station at 10 Vernon Rd, a short walk from downtown. It is served by the Vermonter, a daily train which goes south to New York and Washington, D.C. and north to St. Albans.
- Gallery Walk, . The first Friday of each month from 5:30PM - 8:30PM. Shops and galleries are open and people come to see the sights. A good way to get a feel for the locals. See the fashion show at Twice Upon a Time, a local consignment shop.
- Hooker-Dunham Theater & Gallery, 139 Main Street, . The Hooker-Dunham Theater puts on concerts and dramatic performances. Tickets are usually very reasonably priced. The gallery has an ever-changing selection of art. $.
- Latchis Hotel & Theater, 50 Main Street, ☎ (802) 254-6300 | (800) 798-6301, . A very cool old theater that hosts new films, old films, live theater, and guest speakers. On Halloween they show the Rocky Horror Picture Show, which is great fun. They also show films during the Brattleboro Women's Film Festival. $$.
- Blue Moose Store & Café, 29 High Street, ☎ (802) 246-2000. Mon.-Sat. 10-5, Sun. 9-4. The store sells a variety of cards, kitchen ware, artisan goods, and artwork. Gallery spaces in November and December feature work by several Windham Art Gallery members: Judy Hawkins, Lesley Heathcote, Carolyn Nelson, Marlene OíConnor, Marjorie Sayer, Lori Schreiner, and Robin Stronk. Blue Moose is an ever-changing gift gallery with an artful collection of accents for you and your home. Pottery, blown glass, jewelry, and textiles are complemented by a wide selection of items from cutting-edge European designers and manufacturers. $$$.
- Blue Moose Store & Café, 29 High Street (The cafe is located at the back of the store.), ☎ (802) 254-6245. M-F 8AM-5PM, Sa 10AM-5PM, Su 9AM-4PM. The cafe has the standard assortment of coffee, espresso, and tea, plus a decent selection of gourmet sodas and juices. The baked goods are quite good. The food is great with lots of vegetarian options and is moderately priced. The area is well lit and a good place to read, surf online, or study. The only down side is that they play cheese-ball music. It does not get in the way of conversations or interrupt studying. Cell phone conversations are not encouraged inside the store or cafe, which is nice. Just to reiterate, the music is awful. But it actually helps you do work because you have to block the music out by focusing on what you are doing. The cafe has free wifi with purchase.
- Brattleboro Food Coop (The Coop), 2 Main Street (Near malfunction junction), ☎ 802-257-0236, . The Brattleboro Food Co-op was begun in 1975 as a small buying club. Today, after our November 1997 expansion, the Co-op is a 16,000 square foot supermarket that is enjoyed by the Greater Brattleboro community, member and non-member alike. We are community owned, and so our goal is to be as accessible and responsive to you as possible.We strive to provide you with healthy foods at reasonable prices, in a relaxed and friendly environment. Our staff is knowledgeable and eager to help shoppers in any way that they can. We are located in southeastern Vermont, just over the Massachusetts and New Hampshire borders. Our community offers beautiful Vermont countryside, a lively cultural scene, and easy access to skiing, hiking and other outdoor activities. $$$$.
- Kipling's Restaurant & Pub (Kipling's), 78 Elliot Street (Between McNeill's Brewery and the entrance to the parking garage.), ☎ (802) 257-4848. kitchen: afternoon - evening. Kipling's is a homely little restaurant with a few booths and a bar where you can get a decent burger or the standard pub fare. $$.
- Flat Street Brew Pub (Flat Street), 6 Flat Street (Around the corner from the Latchis), ☎ 802-257-1911, . Restaurant: 5:00 - 9:30. The dining room is adjacent to the Tap Room, both of which are downstairs from the bar. The Tap Room has a great selection of beers. The food is good but not outstanding. $$$.
- Three Stones (Mexican/Mayan Cantina), 105 Canal Street (From downtown, go through malfunction junction and up the hill. The restaurant is on the right just before the stop sign.), ☎ 802.246.1035, . evenings. Maybe the best restaurant, or at least the most interesting restaurant, in Brattleboro. All the food is fantastic and the atmosphere is great. They have a good selection of Mexican cervezas and wines to accompany the amazing food. All the food is authentic Mayan/Mexican food and they use a lot of local and organic ingredients. $$$.
- Amy's Bakery Arts Cafe (Amy's Cafe), 113 Main Street (On the east side of Main Street in the middle of downtown.), ☎ (802) 251-1071, . Amy's has great food and baked goods, plus they have the standard coffee shop items. The area in the back is a nice place to sit and over look the river. Overall, a great place and one of the most popular lunch spots in Brattleboro. $$.
- Fireworks, 73 Main Street, ☎ (802) 254-2073, . 5:30 - 9:00/10:00. Fireworks has the best gourmet pizza in Brattleboro. The bar is a nice place to hang out too. Everything about this place is great. $$$.
- Adagio Trattoria (Adagio's), 132 Main Street, ☎ 802-254-6046, . 11:30 - midnight. Adagio's is the best Italian restaurant in Brattleboro. The bar is nice too. The food is good. $$$.
- T. J. Buckley's, 132 Elliot Street (Past the fire station.), ☎ (802) 257-4922, . By far the fanciest and most elegant dining in Brattleboro. Frommer's even gave the place a solid review. The restaurant is housed in an old diner. The location is a little off the beaten track, but only by a block or two. $$$$$.
- McNeill's Brewery (90 Eliot Street), (The bar is to the left of Kipling's and across from the fire station.), ☎ (802), . Opens at 2pm on the weekends, open until it's closed. McNeill’s Brewery is a full service drinking establishment located in downtown Brattleboro on Elliot Street in an old firehouse that is across the street from the actual firehouse. As for the full service concept, McNeill's provides glasses and will even pour beer into your glass for you for a small charge. They can also put beer in a growler for you (a deal at 10 bones with refills for just 8). They also have some pub food that is better than just edible. And darts. And that game with a ring on a string that you swing and catch on a hook, which is surprisingly difficult even before a few beers. And most importantly, they brew the beer under the floor. No joke! Cash Only. $.
- Flat Street Brew Pub (Flat Street), 6 Flat Street (Around the corner from the Latchis), ☎ 802-257-1911, . 4 pm - last call. One of the trendier bars in Brattleboro, Flat Street has a large selection of beers in the Pub and an even larger selection downstairs in the Tap Room. The bar serves the standard pub fare, but the Tap Room is adjacent to a full dining room. The bar often hosts small concerts. The imperial stout is definitely worth checking out (8.8% ABV). $$.
- Kipling's Restaurant & Pub (Kipling's), 78 Elliot Street (Between McNeill's Brewery and the entrance to the parking garage.), ☎ (802) 257-4848. afternoon - last call. Kipling's has standard pub food and a decent selection of beer. A nice place to stop and get a beer, hang out with friends, etc. Kipling's isn't as trendy as Flat Street Brew Pub and lacks the character and charm of McNeill's, but Kipling's make up for that by being the warmest, friendliest, and most "down-to-earth" bar in Brattleboro. The waitress is really nice too. Cash only. $$.
- The Weathervane, 19 Elliot Street (Between Main Street and the parking garage on the north side of the street.), ☎ (802) 258-6529, . 5 pm - 2 am. The Weathervane is a unique place. They offer live music (sometimes it's a DJ) 5 to 7 nights a week. It's a favorite hangout of Brattleboro townies. The crowd is maybe the most "interesting" in Brattleboro. Brattleboro-ers are an interesting bunch. $$.
- Metropolis Wine Bar, 55 Elliot Street, ☎ (802) 254-1221. Metropolis Wine Bar is a nice spot if you want a cocktail or a glass of wine. Sometimes they have DJ and dancing and sometimes they host art showings. $$.
- Mole's Eye, 4 High Street (Downstairs, under the Brooks building, on the SW corner of Main St. and High St.). Mole's Eye Cafe first opened in 1933, but it closed in 2008. In early 2010, it opened under new ownership and dropped "Cafe" from the name. Now it's just Mole's Eye. They have a pool table, darts, and an interesting game that looks to be a cross between air hockey and pin ball. The beer selection is fine and the food... I've never eaten the food. The worst part of the whole place: if someone doesn't put money into the jukebox, no music plays. I understand having a jukebox and paying for a particular song, but a bar should play music all the time, not just when patrons pay for it. That's lame. Mole's Eye Cafe (the one that closed in 2008) seemed to be a favorite hangout of townies. Mole's Eye (the new one) seems to pick up where the Cafe left off... meaning the crowd is the standard Brattleboro eclectic townie crowd, but maybe a little less "interesting" that the crowd at The Weathervane. And the women's bathroom is nice. $$.
- Latchis Hotel & Theater, 50 Main Street, ☎ (802) 254-6300 • (800) 798-6301, . checkin: 11 am; checkout: 2 pm. Definitely the nicest hotel in Brattleboro. Plus it's right downtown and close to all the good stuff that downtown Brattleboro has to offer. Prices go up on the weekend and during the fall foliage season. $$$.
- The Brattleboro Reformer, . The major local paper.