So, fair enough, the "how" thing might be a little confusing but, if you hadn't noticed, I'm looking for a little continuity here. What "how" means here is a way for you to answer all of the questions that you might ask about B-boro (other than, of course, "How do I get there?" which you can find on the Where page) that start with "How Do I..."
There are a number of bars in town (click here for coffee):
McNeill's Brewery - 90 Elliot Street: Ray McNeill is a great brewer who never misses an opportunity to do more than a little Quality Assurance at the bar. Look for the big guy with the beanie. This is a very basic bar; some imported bar food (from Sarkis down the street), lots of regulars and odd characters, quirky and dark. That said, it's all about the beer and McNeill's serves some whoppers, all under $4.50 (McNeill's also has the best slogan, "Beer is the reason I get up each afternoon.")
Flat Street Brew Pub - 6 Flat Street: Not the same personality as McNeill's but a more upscale feel without a tremendous jump in price. Just opened a restaurant downstairs (check for hours, they're a little spotty right now). Often packed with people from out of town but lively and lots of beers.
There are, of course, many other bars and restaurants with bars in town, but I like beer and I want it to be brewed where I drink it so, as this is my site and not the Frommer's site, I'm gonna let you discover your druthers for drink.
"...find some eats?"
The choices are pretty wide for such a little town. In downtown, there is ethnic food from India, Thailand, Lebanon, the Mediterranean, Asia (Korean/Japanese) yadda yadda yadda. Some highlights are Fireworks (swanky pizza), Riverview Cafe (great view, sit outside, big beers, local food), Shin La, Adagio (nice Italian), Thai Bamboo, India Palace (not pretty but I love me some saag chicken), TJ Buckley's (Supposed to be great but, being only a multi-thousand-aire, I can't afford it), Top of the Hill Grill (bring your own beer and sit outside), and finally the Marina (The kind of place you expect to hear Jimmy Buffett with the outside seating and the view of the water).
"...service a hangover after eating and drinking?"
There are 3 options on the table here:
Go to Bickfords on the corner of Rt. 5 and Rt. 9 north of town. Cheap diner food that is inexpensive and isn't gonna cost you much while also being very affordable for just a little cash without breaking the bank (did I mention that it's food at a great price?). Many will say, "Oh you're crazy! Go to the Chelsea Royal Diner (west of town on Rt. 9)." But the waitstaff at the Chelsea is surly enough to make any hangover blossom.
Go to the Brattleboro Co-op. The oldest Co-op in Vermont and a real "must see" for anyone. It's not flashy, but it is as close as one will come to finding aging hippies in their natural habitat in 2009. They have great produce, prepared foods, and natural products. I'm sure one of the extremely helpful folks there will have "just the thing" for your aching head and flipping stomach.
Sweat it out. On Western Avenue, just east of exit 2, look for Solar Hill on the north side of the street. They have yoga classes there that won't kill you and haven't the attitude that many other studios have. If yoga isn't your thing, park there and go for a walk on the Retreat Trails that have a trailhead behind the building. Great area for mountain biking as well.
"...get some rest?"
Your basic motel options abound in the greater metropolitan area of Brattleboro (that swath being the perimeter made by I-91, the Connecticut river, and Rt. 5). If I were you, I would certainly consider the Latchis Hotel. Truth be told, the rooms aren't super luxurious but the Latchis is upstairs from both the Flat Street Brewpub (mentioned above), making drunk driving less likely, as well as the Latchis Theater where you can watch a film in style (old style, that is). Moreover, the Latchis is on Main street downtown so you can amble around easily.
Brattleboro also has some Bed and Breakfast accommodations available: Forty Putney Road, 1868 Crosby House, the Artist's Loft, and the Meadowlark Inn (not exactly "in town" but close enough). Having previously rented and now owning a home, I can't vouch for these places but they look just swell and if you want more info, that's why the baby Jesus gave us the Internet.
"...soak up some local culture?"
Oh ho ho! This is where The Boro truly shines. One of the top 100 art towns in America and one of the top 10 such towns with a population under 30,000, there is a very thriving local art culture evidenced by the many galleries (which, by the way, have a chance to show off their wares on the first Friday of every month for Gallery Walk). Beyond just art, however, there are practically more used book stores than bars and the New England Youth Theater puts on consistently excellent theater (the founder is a phenom). The New England Center for Circus Arts, The Museum, The Strolling of the Heifers, The Marlboro Music Festival, blah blah blah. Cripes, if you can't find something to do, there's no helping you.
"...get outside?"
Taking a stab at this one, I'm gonna guess that opening a door and stepping through that door are going to be intrinsic to your success in this venture (snarky, no?). That said, once outside, there are quite a few options. There are a number of trails that you can access from town. Here are five favorites:
Wantastiquet: This is actually in New Hampshire but the trail head is about a 10 minute walk from downtown. Go to the southern end of Main street and, at the single worst intersection ever invented (more on this later), take a left and head across the two bridges. After crossing the second bridge, take a left on the dirt road; if you are going into the Walmart parking lot, you've gone too far. Follow the dirt road to its end and start hiking. There are 2 trails here, one goes up and one stays pretty flat. They both continue in the direction they start (i.e. the one the goes up keeps going up and the one that stays flat just cruises along).
The Retreat Trails: The Retreat is a health care facility in Brattleboro. They have an adjoining farm with land holding a wonderful collection of trails. These are great for mountain biking, hiking, snowshoeing, and x-country skiing. I just can't say enough about these trails. Here's my assignment, when you go on the trails, you have to do the following things: find the stone tower, stand at the top of the newly renovated Harris Hill Ski Jump, skip at least one rock on the ice pond, and come out of the trails at least one place other than where you came in.
West River Trail: Go north on Putney road (rt. 5) until you cross the mouth of the West River. Take an immediate left into the parking lot for the kinda ugly pseudo-strip mall. Go around the building and follow it to the Marina restaurant. Take a right instead of going into the Marina's parking lot and park on your right. Follow the road until it becomes a dirt road, then a trail. This is a flat trail that follows the West River for a while and has some nice places to jump in if you're hot. It's an out and back rather than a loop.
Indian Pond: Sorry, New Hampshire again, but this is just stunning. This trail starts at Madame Sherri's Forest which you get to (by car) by taking the first right off of Rt. 9 in New Hampshire after crossing the bridge from Brattleboro. As you take that right, pass the parking lot entrance and take your next left on Gulf road. Keep on that road for a few miles and you'll see the dirt lot for Madame Sherri's on your right. (Get out of your car and) cross the footbridge. Bear left and follow the signs. It's lovely.
Fort Dummer State Park: Lousy name. I mean, really, Dummer? Wow, someone got the crap beat out of them as a kid. Anyway, a really nice little park that has surprised me on a number of occasions. Just go and wander around the trails. It's really nice and, on the off season, very quiet.
"...not sound obnoxious when I ask if there's anything else in Brattleboro?"
Well, in a nutshell, too late. But, if you need more, some random things that are really cool but don't easily fit into the above are:
Mocha Joe's Coffee: For the love o' god, don't start asking around for a Starbucks; you'll be run outta town quicker than you can say, "Iced mocha venti half caf half decaf with a touch of cinnamon light on the ice" blah blah blah. Mocha Joe's is local, cool, and authentically creates the kind of hip cultural experience that Starbucks made a million trying to fabricate in stripmalls everywhere. But wait, there's more: the coffee is black gold and the company uses a lot of farmer-direct coffee (4 x the money to them). Drink without guilt.
Kids Playce: An indoor playground for your progeny. Not too pricey and built for fun. Down the stairs next to the Pharmacy on Elliot street.
The Farmers' Market: During the nice months (May-Oct), this is about a half mile from I-91 heading west off exit 2 every Saturday from 9-2, and outside the Brattleboro Co-op on Wednesdays (Jun-Oct) 10-2. This 35-year Brattleboro tradition offers great produce, great prepared food, great local craftspeople, and a real sense of the community. In this situation, the person who shows up on a bike or walks, is much more badass than the guy in the convertible Corvette; but be careful on Rt. 9, crazy flatlanders are important and must drive fast (vrooom...). BTW, very, very, very kid-friendly.
The Vermont Country Deli: Little pricey? Fine. Horrific parking? Check. But the food and feel of the little red building just west of exit 2 is like "Quaint-Crack" for all the people heading up Rt. 9 (you New Yorkers know who you are). The food is good and the place is never not busy (Sorry, I love a good double negative). Chicken Burritos and Mac-n-Cheese are highly recommended.
The cemeteries: Ok, ok, go ahead and say it. I know you're thinking it. I'm a creep...(and a weirdo). But I've found in my travels that a lot is said about a culture by the way they treat their dead and, although they aren't jaw-droppingly gorgeous cemeteries, they have a lot of history and are worth a wander.
Burrow's Specialized Sports (put on sunglasses before clicking link): Certainly not a bad place but made great by their mechanic, Joe. A very decent guy who, you can tell, loves bikes and isn't out to take anyone to the cleaners.
Experienced Goods: Hate shopping. Love this thrift store. Good cause.
Twice Upon a Time: If you want to buy things that smell like your grandmother, this is the place for you (chuckling to myself, can't help it). Actually, really cool antiques. I'm not into antiques or anything, but it's worth a mention.
Malfunction Junction: For the truly morbid looking for a spectacle, go to the southern end of Main street and feast your eyes on the most poorly designed intersection of all time. It is a miracle that there aren't more accidents.
General freedom: This isn't the name of a place in Brattleboro, it's the wonderfully pervasive attitude of Brattleboro. People have pretty open minds here so if you are a homophobic ditto-head, this may be a little much for you (I'm not saying don't come, just be prepared). That said, if you take a deep breath and fold up your assumptions long enough to experience the place, you may find that it has a unique and genuinely good feeling to it.
"...get more information about this gem of New England?"
Ok, ok, simmer down. I recommend you check out these links, should you have the audacity to think that I've not been exhaustive:
ibrattleboro: Info, forums, jobs, community, events, etc.
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