Located in the Connecticut River Valley, Southampton is in western Massachusetts. The town makes a great base of operations to visit the entire area, and you can be sure to find a great Southampton bed and breakfast or Southampton inn to stay at. You can plan your visit around the Western Mass Comedy Festival during the month of May, or nearby, the Greater Easthampton Fall Festival and Trade Show is a popular fall festival for many locals in the area. When you visit, also check out the Southampton Country Club, which it is a great place to practice your golf swing and enjoy an afternoon of fun in the sun. If you are not a golf fan, consider the Canal Bowling Lanes, which is an economical, family-friendly attraction with reasonable prices. Before you go for dinner, take a nap at a Southampton B&B and then try Opa Opa Steakhouse and Brewery, which offers award-winning brews combined with delicious food. Then for desert, go to Sheldon's Ice Cream for some of the best ice cream in the area. Sheldon's also features deli food. Less