Portland, Maine: Mount Jefferson and Mount Adams via the Great Gulf Trail and Six Husbands Trail
Test out one of the most notoriously difficult trails in New Hampshire's White Mountains.
Portland may be famous for its lobsters, but Maine hikers cherish the seaside city for its its vide variety of trails. Hike along the edge of adjacent Casco Bay as you take in Portland's gorgeous ocean cliffs and lighthouses – or find a paddleboat and experience it from the sea.
But hiking in Portland isn't limited to the city-proper. Drive 20 minutes north to climb up Bradbury Mountain, an easy family-friendly loop that's perfect for a cool Autumn day hike. Backpackers looking for a challenge should head northwest to Maine's White Mountain National Forest. There you can strap on your boots and ascend 2,906-foot Speckled Mountain, a 2,906-foot peak that offers picturesque views of New Hampshire's Mt. Washington.