5 Vacation Destinations For Fall & Winter Hiking

By Marco Barbosa

Just because the temperatures are dropping doesn’t mean that you and the family still can’t hit the great outdoors. From trails that hug the shore of a tiny New England island to treks through the vivid red Arizona desert, lace up your hiking books and hit these vacation destinations for a fall or winter hiking trip.

1. The Berkshires, Massachusetts

The western area of Massachusetts is a wealth of natural beauty, especially its famed fall foliage. For an easy hike that’s perfect for the whole family, head over to the Thomas & Palmer Brook reserve in Great Barrington, where a half-mile trail threads through a meadow and woodlands, offering peeks of large sugar maples and an orchard that are especially gorgeous in the fall. More experienced hikers, meanwhile, can head to Mount Greylock State Reservation, which spans over 10,000 acres. The moderate 6.9-mile Rounds Rock Trek offers the chances to hike through a northern hardwood forest and up to Rounds Rock, where views stretch out across the Berkshires and even father to the Catskill Mountains.

2. Phoenix, Arizona

Hike Phoenix throughout the fall and winter when the days aren’t quite as scorching as the rest of the year, especially in December and January. Check out the Blevins Trail in Usery Mountain Regional Park, where you can spy towering cactuses as you amble the easy 3-mile trail through the Sonoran Desert. Do be sure to pack sunscreen and plenty of water, though, as there’s little shade in this rugged landscape. Minutes from downtown, meanwhile, visit Papago Park where you can wander stunning red sandstone formations among the generally easy terrain.

3. Portland, Maine

Portland boasts the best of both worlds: A vibrant city with a rich art and food scene that’s right on the coast and bordered by hills and mountains. Baxter Woods is a must-visit spot, with the 29-acre lush landscape filled with easy hiking trails, two ponds, and picnic spots. In the fall, head here for birdwatching, while the winter months turn the pine-bordered walking paths into a snowy paradise for cross-country skiing. If you’d rather see the sea, a gentle 1.4-mile trail on Mackworth Island — accessible by car — offers views of the rugged coastline and sandy beaches.

Fall winter hiking

4. San Francisco, California

Looking for some introspection in nature? Philosopher’s Way is a serene 2.7-mile loop around John McLaren Park, and though busy, you’ll find that the crowd is thinner in the fall and winter. Besides the unfolding vistas of Visitacion Valley and the ridges of San Bruno Mountain State Park, the trail boasts 14 “musing stations” crafted in partnership with the San Francisco Arts Commission and the San Francisco Public Utilities Commission. These stations feature plaques with quotes and history meant to inspire a sense of connection to local San Francsico history and ecology.

5. Stowe, Vermont

Few places on the east coast are as breathtaking in the fall as Stowe, Vermont, where the trees are ablaze in reds, yellows, and oranges. The Stowe Pinnacle trail is a moderate 3.6-mile hike up 1,520 feet into the forest and out to the rocky beauty of Camel’s Hump, Mount Mansfield, and more. The trail is aptly named, too. The sights showcased at the top are the pinnacle of beauty of the Green Mountains. A word to the wise: The last section of the trail is quite rocky, so quality hiking boots are a must-pack.

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