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4 of the best special occasion dining options in Brattleboro are:
T.J. Buckleys - a "Chef's Menu" style restaurant located in an old restored train car. Very small, reservations required. Cash or Checks only. Not inexpensive, but worth it. Entrees are about $30ish.
Peter Havens - a Brattleboro favorite, friendly staff and consistently great food. Larger than T.J. Buckleys, but reservations would still be reccommended here. There is a small bar that you can sometimes walk into a seat at. Entrees are about $25ish.
Alici's Bistro - the newest place on the list, has a martini bar downstairs and an outside deck (the only upscale place in Brattleboro with outdoor dining). Reservations are a smart idea here as well, especially if you want to request an outdoor table in the summertime. Entrees are about $22ish.
Capers Restaurant - small, intimate place with a consistent and interesting menu. Can be noisy, but the food and service makes up for it. Small as well, so make a reservation. Entrees are about $22ish.
Brattleboro has a lot of great eateries, but these are the ones that come to mind for "special occasion dining".