The most expensive course on this list makes the cut for one simple reason - it’s an absolute blast to play. Carved out of rocky terrain on the site of FMC Devens, a federal penitentiary that abuts an Army Reserve base (an odd setting that enhances the course’s intrigue), Brian Silva’s Red Tail leaves you breathless on scale alone. The width of its fairways, severity of its contours, and acreage of some of its putting surfaces are duplicated nowhere within the belt of Route 128, and provide dozens of heroic shot opportunities. Conditioning is obviously superb, and the folks in the pro shop may just let you out without a cart to get that price down to two digits, though be warned - it’s a hike.