Casey's Caboose

Casey's Caboose has been serving Killington Road since 1981 out of one of the strip's most genuinely odd landmarks: a 35-ton, circa-1900 railroad snowplow car, retired after a derailment and repurposed into a full steakhouse dining room. It's the kind of story that could easily be a gimmick, but the food has kept locals and visiting skiers coming back for over four decades. The menu leans classic steakhouse — hand-cut steaks, prime rib, and a full raw bar — alongside a well-stocked bar scene that makes it a regular après stop as much as a dinner destination. It's currently rated the #1 restaurant in Killington on TripAdvisor, a distinction that's held up across hundreds of reviews. Casey's Caboose is also genuinely dog-friendly, a detail that stands out on a strip where that's not the norm — worth knowing if the trip includes a four-legged member of the party. Open nightly, it's an easy, reliable pick for a proper sit-down dinner without needing to plan far ahead.

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