We rented a house for this weekend in Brattleboro and will be driving there from Boston.
Any ideas or suggestions of fun things to do in the area? Any great restaurants or towns nearby? We are celebrating my friends 30th birthday!!

Really enjoyed a meal at Peter Havens last September. http://peterhavens.com/

T. J, Buckleys http://www.tjbuckleys.com/ is supposed to be very good as well.

The Marina http://www.vermontmarina.com/ has a lively bar scene and decent pub grub.

You might want to explore Keene. We've enjoyed lunch at Luca's. Looked like there are some interesting bookstores in Brattleboro.

this is great! Thank you! Any fun activities like a great hike or cute stores or anything to do with maple syrup with a group of 15 women!

http://www.stuartandjohns.com/ is a sugarhouse restaurant about 20 minutes form Brattleboro, it should be a beautiful drive.
In town is Paradise farm with Maple products but no hot breakfast.
Most of Brattleboro is filled with "cute" stores, the downtown is small so not hard to find anything.

For good but not cheap dinner TJ Buckley is great but 15 is about their capacity so you would definitely have to reserve.

Three is new snow so snowshoeing or skiing will work better than hiking!

We are expecting 8" of snow today, and it will be in the high 30's this weekend, so it will be somewhat wintery. Snowshoeing might be a fun thing to do. Since I live about 60 miles north of Brattleboro, I don't know specific snowshoe trails in that area, but I'm sure there are plenty. Stop in one of the local bike/ski shops in town, they can fill you in and probably rent you gear. Of course you could always spend a day skiing at someplace like Mt Snow or Magic Mountain.
If you want to do some shopping, Basketville in Putney is fun - a huge building filled with baskets, local foods, souveneers, furniture, even a wine tasting room. Also don't miss Sams in downtown Brattleboro, a sprawling multi floor store packed with outdoorsy clothing, shoes, sporting goods, etc.
Our favorite place to eat in Brattleboro is the Thai Bamboo in downtown - one of the best Thai restaurants in northern New England. Even though Brattleboro is considered a 'big city' (with a bohemian vibe) in Vermont, a 10 minute drive on some back roads will take you into beautiful Vermont countryside.

Thank you Zoots and Jubilada! I think Thai sounds wonderful as we would like to watch the budget Snowshoeing sounds fun too.....WOW 8" in Boston it was 2 and slushy! Should be magical I think. Thank you for the store info. Should keep us busy for awhile!!

Try on Retro clothing at "Second Time Around". Try beer and ale samplers at the Flat Street Brewery. Check out the Hooker Dunham Theater to see if they have any activities. Get your Tarot read at the fun little shop up the hill next to a ticketed parking lot (sorry, can't recall the name, but he lady and her dog are super-nice).