Hiking Trails
Near Great Barrington, Massachusetts

Discover the must-do hikes in the area, handpicked and curated by local experts who know the trails best. These routes are beloved for good reason, offering standout scenery, rewarding terrain, and detailed descriptions with tips that tell you exactly what to expect. Whether you are visiting for the first time or are a local doing them on repeat, they offer a reliable and memorable hiking experience.

These hikes keep it under 5 miles and climb less than 1,500 feet, making them ideal for quicker outings or lower-key days. Perfect for a morning stretch, a casual afternoon, or getting outside without committing to a big push. Don’t let the stats fool you — many still pack in great views and rewarding moments.

Not finding what you're looking for? These additional nearby hikes offer more ways to get outside and explore the area. With a mix of lengths, difficulty levels, and terrain, you're likely to find something that fits your plans for the day. And remember, you can always use the onX Route Builder to create your own adventure from scratch.