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. $$.
- Brattleboro Farmer's Market, (Saturday Market: Take exit 2 from I91, turn west on Rt. 9. Market is .5 mile on the left just past the Creamery Covered Bridge. Wednesday Market: From I 91 exit 2 turn east on Rt. 9. Follow to the ‘T’ on Main Street, turn left, Market is .25 mile on the right , next to the Gibson-Aiken Center.), . Saturday & Wednesday. The Brattleboro Area Farmers' Market is Southern Vermont's premier farmers' market featuring over 50 vendors with agricultural products, crafts, live music and animals and ethnic foods from around the world. Whether you are local or a tourist, you can stop by to get your weekly produce and grab a quick lunch, or come with your family and stay for the day! In the winter the market is held in the River Garden on Main Street in downtown Brattleboro. $$.
- 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, . Healthy foods at reasonable prices, in a relaxed and friendly environment. Staff is knowledgeable and eager to help shoppers in any way that they can.
- 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. The restaurant is housed in an old diner. The location is a little off the beaten track, but only by a block or two.
- Top of the Hill Grill, 632 Putney Road Brattleboro, ☎ (802) 258-9178, . lunch & dinner. Top of the Hill Grill serves hickory smoked beef brisket, pulled pork and ribs, smoked turkey, grilled chicken and fresh ground burgers. Also, homemade sides – always from scratch and always fresh – include coleslaw, corn bread, baked beans, roasted potatoes and root vegetables, pasta and potato salad. Great BBQ.
- The Chelsea Royal Diner, 487 Marlboro Road Brattleboro (To get here, take exit 2 off Route 91 to Route 9 West, drive 2 miles. Just when you think you've passed the Royal Diner it will appear on your right. Remember the best part of The Royal Diners' location, just outside of Brattleboro, is that you have to pass it on the way up to Vermont and on the way home.), ☎ (802) 254-8399, . breakfast, lunch, & dinner. A vintage 1938 Worcester diner. Decor and food speak of times gone by with Daily Blue Plate Specials, generous portions and extremely friendly pricing. The cuisine is probably best described as "high-end home style". Authentic Mexican fare served Tuesday through Saturday evenings, prime rib Friday and Saturday nights, real mashed potatoes, homemade soups, breads, pies and desserts. Breakfast is served all day and they are a feast, with homemade pancakes and Belgian waffles, eggs Benedict, and the Diners' specialty "Cajun Breakfast Skillet" make for some tough choices. The menu also offers an array of sandwiches, pizza, and a kids menu. Take-out is available for every item. April through October is the season for the Royal Soft Serve Stand, featuring Columbo Nonfat Frozen Yogurt, 10 flavors of Soft-Serve daily, and the Royal's Homemade "Royal Madness" Ice Cream. There's lots of classic eats too, such as footlong hotsogs with fries, and double cheese burgers.
- Elliott Street Cafe, 134 Elliot Street, Brattleboro, VT (Up Elliott St., past the fire station, on the left), ☎ (802) 246-1251. breakfast, lunch. Great Mexican inspired breakfast and lunch. Very basic set up, very good food. Lots of vegetarian options. They cook all their dishes from scratch, with the highest quality / local ingredients they can find, and lots of love! They are committed to supporting local, sustainable food systems, and a strong local economy. They also have ping pong and host performances.
- 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.
- 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 St (downstairs, under the Brooks building, on the SW corner of Main St and High St). First opened in 1933, but it closed in 2008. In early 2010, it opened under new ownership. 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. The worst part of the whole place: if someone does not put money into the jukebox, no music plays. The crowd is the standard Brattleboro eclectic townie crowd.
- 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.