I will be coming up from Long Island for a few days the weekend of 9/24..I have never been to Vermont and was looking for some things to do around Mt. Snow.  Me and my girlfriend are in our 30's if that helps any.

Manchester for shopping outlets, Orvis and spending huge sums of money in "boutique" shops. Sounds great doesn't it ???
Or ... get your non-resident license online, print it out, bring your shotgun and leave her in Manchester. Then, head for the Nat'l Forest (access up the mountain just South of Manchester off Rte 7).
Grouse season will be open... have a ball exploring the forest. How's that for something to do ???

There's great hiking, fishing, mountain biking, etc.  Can you give some us some ideas of your interests so that we can give sonme informed suggestions?

museums, historical sites, outdoor, etc...

Bennington battle monument?

wait a couple months and you can ride the hills

Eat at The Hermitage, right down the road from Mt Snow.  Very nice, classy, fine dining.  

Manchester offers the Factory Outlets as well as a variety of local shops and antique stores. Brattleboro contains the state’s first settlement, Fort Dummer, located in the Vermont State Park. Bennington also offers many historic sites as well.  

Sun Mountain Adventure Park
Rte 11
Manchester, VT
Ph:  (802) 824-5522
Alpine slide, water slide ride, mini golf and more.

Southern Vermont Arts Center
West Road
Manchester, VT
Ph:  (802) 362-1405
National Historic trust mansion filled with contemporary art, galleries, and rotating exhibitions.  

Hildene
Rte 7A, 1005 Hildene Road
Manchester, VT
Ph:  (802) 362-1788.
Tour Hildene, the home of Abraham Lincoln's descendents until 1975.  Georgian Revival Mansion with original furnishings.

Historic Grafton Village
Rte 121
Grafton, VT
Ph:  (802) 843-2255.
Restored 19th century community.  Fine example of rural New England architecture and village life.  Self-guided tours.  

Green Mountain Flyer Scenic Train Ride
Chester Depot
Bellows Falls, VT
Ph:  (802) 463-3069
26 mile excursion train with restored coaches pulled by vintage diesels.

Basketville
Rte 5
Putney, VT
Ph: 802-387-5509.
World class collection of baskets, home accessories, wicker furniture, old fashioned toys and silk flowers.  

Brattleboro Museum & Art Center -
Union Railroad Station
Brattleboro, VT
Ph:  (802) 257-0124.
Series of rotating yearly exhibits.

North River Winery
Rte 112
Jacksonville, VT
Ph:  (802) 368-7557.
Tours and tasting of award wining wines at one of the most scenic wineries on the East Coast.

Stratton Mountain Village & Gondola
Stratton, Mountain, VT
Ph: (802) 297-2200.
Stratton Mountain resort offers many attractions for many interests.

The food at 2 Tannery Road is very good.  I stay at the Snow Goose Inn with my wife for our anniversary every year.  

West Dover is a nice area.  We were considering moving somewhere around there since it's the same distance for me to work.  Unfortunately, my wife just isn't ready for the move yet.  Maybe after my daughter is done with high school.