Pros

• Beautiful scenery + outdoor access
  Southern Vermont is classic New England: forests, rivers, hiking, fall foliage, kayaking, skiing nearby, and quiet roads. The Connecticut River area is especially pretty.
• Small-town community feel
  A lot of residents like the slower pace and tight-knit vibe. You’ll probably recognize people around town fairly quickly. Community arts/events are a real thing there.
• More affordable than much of Vermont
  Compared with Burlington-area prices, Rockingham is relatively affordable. Median home values are lower than national averages on some rankings.
• Historic character
  Bellows Falls especially has old brick mill-town architecture and a distinct personality. Rockingham has a lot of pre-WWII homes and historic buildings.
• Good for remote workers or retirees
  If you work from home or want quiet living, it can work really well. Telecommuting rates are relatively high for a small town.
• Access to NH + regional cities
  You’re not isolated from civilization — Keene, Brattleboro, and parts of New Hampshire are reachable, and I-91 helps with travel.
• Artsy / creative culture
  The town reportedly has an unusually high concentration of artists and creative professionals.

Cons

• Limited jobs locally
  This is probably the biggest practical downside. Unless you work remotely, healthcare, trades, education, or small business, job options can feel thin.
• Winters are long and serious
  Vermont winter isn’t “cute snow” after month four. Ice, mud season, heating costs, snow tires, and dark afternoons wear some people down.
• Healthcare and services can be limited
  Rural Vermont in general struggles with specialist access and convenience. Residents on Reddit often complain about long drives for medical care and fewer amenities.
• Quiet can become “nothing to do”
  If you want nightlife, major shopping, lots of restaurants, or frequent entertainment, you may get bored. Things close early, and options are limited compared with metro areas.
• School quality is mixed
  Schools aren’t considered terrible overall, but they’re not usually viewed as a major draw either. Some local schools have middling ratings.
• Some economic roughness in Bellows Falls
  Bellows Falls has charm, but also visible poverty and some drug/crime concerns compared with more affluent Vermont towns. Crime overall is moderate, though property crime is relatively low.
• Housing inventory can be tight
  Even when prices are lower than other Vermont areas, availability is limited. Rural Vermont housing shortages are a recurring complaint.

Who usually likes Rockingham?

• Remote workers
• Retirees
• Outdoorsy people
• Artists / creatives
• People wanting quieter, cheaper New England living
• Folks okay with rural inconvenience

Who may struggle there?

• People needing strong career growth locally
• Big-city social personalities
• Anyone who hates winter
• People wanting diversity of food/shopping/nightlife
• Families prioritizing top-tier schools

Overall, Rockingham is more “authentic Vermont mill-town with character” than polished postcard Vermont. For some people that’s exactly the appeal.