Chester does have it's fair share of hospitality based industry:
Chester Vermont Innkeepers Association - Lodging and Accommodations in the Okemo Valley Region and that doesn't even list the smaller B&Bs. With Chester relatively close by, a savvy person in the hospitality industry would have to create a special niche.
Londonderry does have a great farmers market at the junction of Rte 100 & Rte 11 every Saturday from May through October. The crowds are phenomenal.
Just outside in Bondville there is the annual Bondville Fair (this year Aug 28-30). It is billed as the oldest continuous running fair in VT.
Bromley has a summer outdoors park which attracts families with all sorts of hands on, physical recreation/amusments.
Going back to ski areas, depending upon where the location is in Londonderry -- Okemo isn't a bad run up 100.
Golfing: there's golf off Rte 11 in the far western reaches of Chester there's Tater Hill, several courses in Manchester and the Okemo Valley GC in Ludlow.
Fishing: You'll be close to the Battenkill and over in Manchester it the flagship store for the fly fishing Mecca which is Orvis.
Shopping: Send the men golfing and fishing and the ladies can shop til they drop in Manchester at the scores of outlets.