1. What trails do you recommend for beginners?
To start getting a feel for the up and down challenge of mountain hiking, some gentle hills close to Boston , including Moose Hill in Sharon, MA (part of the Moose Hill Audubon Center) and Noanet Peak, part of Noanet Woodlands in Dover, MA, make for good practice. For a flatter, but still challenging hike, try Blueberry Hill and the Discover Hamilton Trail, both in Bradley Palmer State Park. An extra perk for novice hikers in New England: almost all of Cape Cod and Rhode Island, with their relatively flat terrain, are perfect for beginners.
2. Is Walden Pond worth a visit for literature enthusiasts?
For literature enthusiasts, yes. Fans of Walden can see a replica of Thoreau’s original cabin (located near the state park’s parking area) and then, while out on the hike, visit the actual site, marked by a sign and a giant pile of rocks. It can be a thrill to hear the same types of birdcall, smell the same scent of pine, and see the same shimmering water Thoreau did almost two centuries ago. Because the place is often packed on summer weekends (thanks to the eternal draw of Thoreau and the fact that there is a very nice swimming beach at Walden Pond ), try visiting early in the morning in order to avoid the crowds.
3. Where can hikers find the most striking view?
For breathtaking views back towards Boston, nothing beats the Blue Hills Reservation’s Skyline Trail in Milton. For stunning water views, try Great Island Trail and Province Lands Trail on Cape Cod . For both water and city, take the ferry out to the Boston Harbor Islands, home to some unusual hiking opportunities and uniquely stunning vistas. For that traditional mountaintop view of rolling countryside, visit Bauneg Beg Mountain and Mount Agamenticus, both in southern Maine. From these two hills, views stretch all the way to Mount Washington!
4. What hikes do you recommend with historical significance?
Boston is known for its history  and hikes that take you to significant places from the past are in no short supply. One of the highlights is Battle Road in Concord and Lexington, a gravel path that winds along the original route the Minutemen and Redcoats took during the opening battle of the American Revolution in April 1775. You can even visit the spot where Paul Revere was captured during his famous midnight ride.
5. What trail do you consider a best-kept secret?
Again and again, I’m drawn to Dogtown Woods in Gloucester, Mass. It’s a rambling woods walk that takes you past the remains of an old Colonial settlement that was abruptly abandoned in the 1700s. The people left in such a rush, so the legend goes, that they left their dogs behind, giving the place its moniker. The other curiosity of Dogtown is the Babson Boulders, a series of massive glacial erratics that an eccentric millionaire carved inspirational sayings into during the Great Depression. Short spur trails lead you to read such phrases as, “Get a Job” and “Never Try, Never Win”. Some say Dogtown is haunted. I’ve never seen any ghosts there (or many people, for that matter), but agree that the woods possess a very spooky, haunted feel.
6. Name two trails that are good for hiking with kids.
I have two kids and on most weekends you can find us out on the trail, exploring interesting terrain in places like the critter-filled woods of Beaver Brook Reservation in Hollis, NH and seaside Odiorne Point in Rye, NH. Kids will keep hiking when they know the pay-off is experiencing something unique and exciting. For my kids, these two places fit the bill—over and over and over again.
7. What kind of wildlife might hikers encounter?
Moose and bear call the woods of northern New England  home, meaning that for “big animal” sighting, try forest hikes in New Hampshire and Maine. Throughout all of New England, you might come in contact with any one of a number of critters, including opossum, woodchuck, chipmunk, fisher cat, beaver, muskrat, bobcat, red fox, and white-tailed deer. Closer to the coast, look for harbor seals (especially off the coast of Maine). Notable bird species in the region include great blue heron, wild turkey, red tailed hawk, peregrine falcon, bald eagle, screech owl, barn owl, Baltimore oriole, grackle, black-capped chickadee, and northern cardinal.
8. Is it easy for city-dwelling Bostonians to escape the urban landscape and find a hiking spot close to home?
Absolutely! When I first moved to Boston, I didn’t own a car, but still managed to get out on the trail most weekends. If you’re savvy with MBTA and Commuter Rail scheduling, you can get yourself to World’s End in Hingham, Walden Woods in Concord, Battle Road in Concord and Lexington, Eastern Prom in Portland, ME, points on Cape Cod and Block Island and Newport in Rhode Island .
9. What hike do you consider the most challenging?
The trip up 5260-ft. Mount Lafayette, part of the Franconia Ridge in the White Mountains of New Hampshire, is pure, rugged mountain adventure. Climbing into a true alpine zone, the views down into Franconia Notch and beyond and unforgettable. If you’re in good shape, go for it! Truly hardy souls can combine Mount Lafayette with a visit to neighboring Mount Lincoln (another 5,000-footer) for a truly advanced loop hike.
10. What’s the best time to plan an extended hiking trip in the Boston area?
The end of June is just about perfect in New England. The days are pleasant, the mud season has dried up, and the mosquito population has yet to peak (though black flies can be heavy in June). For those combining camping and hiking, June is also perfect for having your pick of campgrounds that are booked solid in July and August. If you’re coming to New England for the fall color, try the weekend BEFORE Columbus Day for the same brilliant hues, without the crowds.