Okemo's Fall into Winter festival is on Sunday at the Jackson Gore base. They have live music, a cider bar, mountain coaster rides, pumpkin decorating, and more from 12pm-5pm.
Quick hike down, a bit more strenuous on the way back up. You can also view the gorge from the road and get a spectacular view of the foliage. This is a very popular tourist spot during leaf season so you're better off visiting in the morning or the late afternoon.
Fun Irish pub in Ludlow with great food and great service. Make sure to check out the specials menu, but the corned beef is always A+. Try and find my dad's East Windsor PD patch above the bar!
Fancy little upscale cocktail bar with snacks. Outdoor seating area is heated and stays pretty warm in the evenings, don't be afraid to sit outside!
Awesome late-night hang out spot near downtown Ludlow and the base of Okemo. Max's band played here over the summer!
One of the coolest antique shops in New England. This is a destination stop for many people in the antiquing community. Last time we went, a carload of people pulled in next to us saying they had driven 6 hours to get there.
Open 10a-5p daily. This museum preserves the birthplace and longtime home of President Calvin Coolidge. His family founded the Plymouth Cheese Factory, which still operates today and has a shop nearby that continues to sell America's oldest cheddar. You can also find Plymouth Cheese in grocery stores, its wax casing helps the cheese stay fresh outside of the fridge for quite a while (it's safe to drive home with!!)