Favorite Late-Fall Hikes

Autumn was slow to arrive this year; September was balmy, and October barely chilly. But the trademark halcyon skies, crisp air, and warm sun of the New England fall has finally shown up, bringing with them the old familiar sense of seasonal urgency: Must! Hike! Before! Winter!


The northwoods hiking season properly ends Columbus Day; many hiker conveniences close up as ice begins to form on the summits of New England’s 64 four-thousand-footers, and unless you’re a serious mountaineer, I don’t recommend flirting with the big peaks this late in the year. Four thousand feet may not sound like much (when there are fourteeners in the Rockies), and when the closest are just a two-hour drive from 60-degree Boston, it can be tempting to try and extend the season. But the weather in the inland mountains is a very different beast than the weather in the coastal city. One rule of thumb says that every 1000 feet of elevation gain is like being 300 miles further north. So the summit of Mount Washington is the equivalent, temperature-wise, of being 1,800 miles north of Boston — that’s roughly the northern coast of Iceland. (Much of my respect for mountain weather has been informed by my own mistakes, and sharpened by tales of disaster detailed in the highly readable Not Without Peril: 150 Years of Misadventure on the Presidential Range of New Hampshire. The title conveys my gist.)

Fine views can still be had at lower elevations.

But perhaps I can interest you in a number of excellent hikes and woodland rambles that are either less in elevation or more southerly, and hence better candidates for late fall excursions. I’ve organized them by the amount of time they take as a trip from Boston:

Half a day: The Middlesex Fells and the Blue Hills are your best bet for a quick dose of forest-time. The former is a quick drive north of Boston on 93; the latter, just to the south. The Fells are a great place to bring your dog to play with other pups at the Sheepfold, and offer a somewhat disorganized network of paths to ramble around (note: I bought the map and found it useless). The Blue Hills have great hiking and mountainbiking trails and a mapping system that’s actually legible.

Now, if by “hike” you really just mean, “walking around in nature,” my favorite fall spot may be Walden Pond, about half an hour from Beantown. The hordes of summer swimmers will have dissipated, and you can contemplate in peace the quotation from Thoreau installed on a sign next to his cabin site: “I went to the woods because I wanted to live deliberately, to front only the essential facts of life… and not, when I came to die, discover that I had not lived.” And if you get an Indian Summer day, why not dive in? (I swam across one warm October day a few years ago, and I felt tingly the whole way home. I learned later that some consider this an early sign of hypothermia.)

More resources: AMC’s Best Day Hikes Near Boston.

Three-quarters of a day: About 90 minutes from Boston out Route 2, you’ll find Mount Wachusett in the town of Princeton. The highest point in Central Mass, you can be up and down in about 45 minutes if you take the shortest, steepest route. That makes this a good option for people with young children (I was three years old the first time I hiked this glorified hill). Adding a scenic drive through Massachusetts’ apple belt makes this a complete day out. It’s late in the season for apple picking, but a great time for pumpkin picking. Or for posing your moppet on a heap of pumpkins for that classic New England toddler portrait.

There’s a view there…somewhere.

Mount Monadnock, a peak in southern New Hampshire roughly two hours from Boston, has a rep for always being crowded, but this late in the year I’ve found it pretty empty. Maybe that’s because I’ve always gone on drizzly, foggy days. The most popular route, the White Dot Trail, offers an athletic bit of scrambling towards the summit, which has great views. If you go, I recommend taking 119 on the way back; it’s a pretty country road and will take you to a classic family restaurant from my childhood, the atmospheric Johnson’s Drive In.

More resources: 60 Hikes Within 60 Miles: Boston.

All day: Head out I-90 or Route 2 and get thee to the Berkshires. Because I’ve been busily trying to collect New Hampshire’s 48 four-thousand-footers, I’m admittedly guilty of ignoring the summits in my own backyard. But there’s 90 miles of Appalachian Trail out there to explore! I found this website particularly useful — a quick search for outdoor/adventure activities in the Berkshires gave me two new options to try: the Becket Land Trust Historic Quarry and Forest and the amazingly named Bartholomew’s Cobble.

(Note that the regions west of Boston are predicted to get 1-3 inches of snow accumulation today; if you hit the Berkshires this weekend, bring your Bean Boots.)

It’s an austere beauty.

Alternatively, you could combine a scenic drive around New Hampshire with one of the hikes right off the Kanc (NH 112). A straight, flat trail with almost no elevation gain is the Lincoln Woods trail, running alongside the Pemigewasset River for much of its length. You could also head up either the Avalon or the Mt Willard Trail from 302 (they both leave from the AMC Highland Center at Crawford Notch) and hike to your first good vista.

More resources: AMC’s Best Day Hikes in the White Mountains.

Hike the Camden Hills and get a great view of Camden Harbor.

All weekend: The Camden Hills, right behind Camden, Maine are covered with trails leading up to a classic view — Camden’s picture-perfect harbor. The coastal location and relatively low elevation mean that you’re unlikely to come across severe snow or ice this time of year. Still, hike prepared. It’s a good three-and-a-half hour drive from Boston without stopping — but when you can break up the trip with a sampler of Smuttynose beers and a warm pretzel roll at the Portsmouth Brewery (an hour from Boston) or any of the fine eateries of Portland, Maine (two hours), why would you do that to yourself?

More resources: Moon New England Hiking: The Complete Guide to More Than 400 of the Best Hikes in New England.

We’re always looking for new favorite hikes, so please let us know what we’re missing in the comments!

2 thoughts on “Favorite Late-Fall Hikes

  1. Christine says:

    I finally went up Mt. Battie in Camden this summer– a delightful hike with a beautiful view of the harbor as your reward for making it to the top.

    Hopefully, we get one more nice fall day before winter sets in so I can try out some of your suggestions!

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