Take Route 2 East to Route 140 North (Exit 24 Westminster/Winchendon), turning left at the end of the exit ramp. Drive approximately three miles to Route 101 North. Turn right onto Route 101 and follow it approximately four miles to the Academy. Turn left onto Pleasant Street. Turn left onto Academy Street. Welcome to Cushing Academy!

Exit the airport and drive through the Ted Williams Tunnel. When exiting the tunnel, continue on I-90 West for approximately 10 miles to Exit 15, the third tollbooth from the airport. Stay to the right. Take I-95 North for approximately 6.3 miles to Exit 29B. Turn right on to Route 2 West for approximately 39 miles to Route 140 North (Exit 24B Winchendon/Ashburnham). Drive approximately three miles to Route 101 North. Turn right onto Route 101 and follow it approximately four miles to the Academy. Turn left onto Pleasant Street. Turn left onto Academy Street. Welcome to Cushing Academy!

Take I-84 from Hartford and travel East to I-90 (Massachusetts Turnpike). Follow the Mass Pike East for 10 miles to I-290 East (towards Worcester) to I-190 North (towards Fitchburg). From I-190 North take Route 2 West to Route 140 North (Exit 24B Winchendon/Ashburnham). Drive approximately three miles to Route 101 North. Turn right onto Route 101 and follow it approximately four miles to the Academy. Turn left onto Pleasant Street. Turn left onto Academy Street. Welcome to Cushing Academy!

Take a right out of the airport onto Brown Avenue. Following Brown Avenue you will pass an industrial park on your left and a McDonald's on your right. After driving under both overpasses, take an immediate left at the traffic light. Signs at this light will say left for Route 293 North and Route 101. Route 293 will split off to the right, but you will stay to the left and follow signs for Route 101. Take a left at the light onto Route 101 West. Follow 101 West approximately 16 miles until your reach Route 13 South. Follow Route 13 South for approximately 12 miles to Route 119 West. After approximately 10 miles, turn left onto Route 101 South. Cushing Academy will be on your right on Route 101 South just after you pass through the center of Ashburnham. Turn left onto Pleasant Street. Turn left onto Academy Street. Welcome to Cushing Academy!