Walk in the Footsteps of Authors: New England’s Best Literary Hikes

Ashley recently assigned herself a reading syllabus of New England authors and then took a road trip, hiking many of the authors’ favorite trails. In this guest post, she shares with us the best of New England’s literary hikes. 

There’s an image of writing that circulates in our collective brains; the grizzled writer walking off into a field with his notebook and a nubby pencil, to sit in the setting sun and wait for inspiration to strike. A few bird chirps later and out pops a naturalist literary masterpiece.

I don’t know about you, but the last time I took my grand ideas of literary genius into the woods, I emerged with more mosquito bites than lines of prose. Personal experience aside, there’s something to this idea about writing and nature that persists. In the US it probably originated with our beloved early American New England writers. The Transcendentalists come to mind, naturally 😉. They made crafting naturalist masterpieces out of bird chirps and the last rays of sunset seem easy. But I’ve taken enough hikes to inspiring vistas and shimmering lakes and returned empty-handed enough to know that New England and the Transcendentalists had a special relationship.

After a long road trip through New England’s most literary regions (call it a literary pilgrimage), I get it. The place is gorgeous, y’all, and thankfully, blessedly, much of New England’s literary landscape has been preserved. You can actually walk where America’s most famous authors walked, breathe the same air, and if you’re lucky, glean a little writerly inspiration for yourself.

Want to take your own literary pilgrimage? Good news — I’ve narrowed down New England’s best literary hikes for you!

Monument Mountain

Great Barrington, Massachusetts

It’s true that Nathaniel Hawthorne, Herman Melville, and William Cullen Bryant took annual picnics to the top of Monument Mountain in Great Barrington, MA, and the stories told about these trips have reached epic (well, to a bunch of English majors anyway) proportions. According to Bernard A. Drew, Hawthorne and Melville met for the first time during a trip up Monument Mountain in 1850. Hawthorne was moody and irritable the entire trip, while Melville, who had begun writing Moby Dick earlier in the year, was acting the role of a jaunty sea captain at every overlook. Bryant, fed up with their antics, got drunk on champagne, and almost fell off a cliff.

Monument Mountain is a great hike even without this backstory, but knowing the absurdity of that trip in 1850 makes it even more enjoyable. The trail is rocky and a bit steep in places, but the gorgeous views over the valley below are well worth it. I recommend taking Indian Monument Trail until it intersects with Squaw Peak Trail up to the top (with a stop at Devils Pulpit along the way–the views are incredible), then taking Hickey Trail down again. Monument Trail is a slow and steady route, while Hickey Trail is rockier and steeper. It’s a loop so you could take either direction.

If you don’t pause at the top to read an excerpt of William Cullen Bryant’s “Monument Mountain” (and to drink a mini-bottle of champagne in these three authors’ honor) then we’re not the kind of people who can be friends.

Robert Frost Stone House

Shaftsbury, Vermont

If you’re in Vermont, you can’t throw a rock (or an apple if it’s October) without hitting a house that once belonged to Robert Frost, but Stone House is my favorite. He lived there in the 1920s, and it’s where he penned “Stopping By Woods on a Snowy Evening.” Definitely take time to explore the house itself, but the real treasure is outside. If you’re short on time there’s a quick jaunt around the property line, but at the edge of the property is the start of a 3.1 mile (round trip) hike down to Lake Paran and back. The Robert Frost Trail (it’s on All Trails as the Paran-Frost Trail) is great for varied scenery (there are a few small creek crossings but nothing difficult), and the Stone House side of the trail passes through a pine grove planted by the poet himself.

Insider’s tip: pick up a delightfully illustrated tree identification guide (drawn by Sophie Parker-Goos) to take with you as you hike!

Mt. Greylock

Berkshire County, Massachusetts

If New England has one literary holy site, that site has to be Mt. Greylock. Its craggy face appears in writing by Nathaniel Hawthorne, Henry David Thoreau, and Oliver Wendell Holmes. Most famously, it was a snow-covered Mt. Greylock that Herman Melville saw from his study window and inspired him to write about a certain white whale. Most recently, J.K. Rowling set her American wizard school on Mt. Greylock’s peak. (I tried really hard to find the entrance to Ilvermorny but failed. I’m still mad about it.)

Mt. Greylock has trails for every hiker. The shortest is less than half a mile, the longest is over 13. The Appalachian Trail passes through Mt. Greylock if you have a Bucket List item you’d like to check off. If you’re more bohemian in your planning, I recommend driving the road to Mt. Greylock Observation tower and stopping at whatever trail crossing strikes your fancy (there’s parking along the way).

Robert Frost Wayside Trail

Ripton, Vermont

After several days of long, steep hikes, you’ll probably want a rest day, and there’s no better place than bucolic Ripton, Vermont. Robert Frost lived in a cabin at the Homer Noble Farm while he taught at the Middlebury Bread Loaf school for over 20 years. The cabin isn’t open to the public, but you can walk the fields around it. And they are beautiful fields, and quieter than any other literary site we visited on our trip. Our only companion was a feisty chipmunk who guarded the path to Frost’s cabin from his burrow in a stone wall that lines the path.

Across the road from the Homer Noble property is the Robert Frost Interpretive Trail. This is a short (1.2 mile), mostly flat nature trail peppered with markers engraved with Robert Frost’s poems. You won’t be out of place at all if you stop to read poetry aloud, and there are several good places to stop for a picnic lunch (either on the trail itself, on the Homer Noble Farm, or at the nearby Robert Frost Wayside area). I loved this trail for its varied scenery–you walk through hardwoods, an open field, and along a river all in one short trek.

Walden Pond

Concord, Massachusetts

Walden Pond is perhaps the best known pond in the world, and I’m glad it’s a site people can enjoy today. The lake itself is a popular attraction. In the summer months and on holiday weekends the park frequently reaches capacity with swimmers and boaters, so check the park’s hours (they’re based on sunrise and sunset) and plan to arrive a bit before park opening to be guaranteed entrance.

There’s a network of trails that surround the lake, and it’s inspiring and a little humbling to walk the steps that Concord’s Transcendentalist greats took. The most travelled trails are the one around Walden Pond itself, and the path to the site of Thoreau’s cabin.

The trail around Walden Pond is 1.7 miles and nearly flat. There are several access points to the pond as well for a mid-hike break to dip your toes. The trail to Thoreau’s cabin site is just another 5-10 minutes from the pond, and the cabin site is marked by granite pillars. Hikers bring stones to add to the cairns in tribute to Thoreau, so be sure to bring one as well. It’s not strictly leave no trace, but it’s been a tradition since 1872 when Bronson Alcott (Lousia May Alcott’s father and leader in the Transcendentalist community) brought his friend Mary Newbury Adams to the site, who left the first stone.

There are many additional trails at Walden Pond State Reservation that could take a couple of days to fully explore. The woods are more piney than in surrounding areas, but the history of the place is worth each pine cone riddled step. Check the visitors’ center for guided hikes and literary presentations after you visit the recreation of Thoreau’s cabin (somewhat strangely placed between two parking lots).

–> Read more about visiting Walden Pond

The Emerson-Thoreau Amble

Concord, Massachusetts

Oddly, my favorite hikes at Walden Pond isn’t near the pond itself, nor is it much of a hike. But the 1.7 mile, nearly entirely flat Emerson-Thoreau Amble is a gem of a trail that connects Henry David Thoreau’s cabin to Ralph Waldo Emerson’s back door. Emerson and Thoreau were close friends whose lives intersected both on and off the page. It was Emerson’s land on which Thoreau built his cabin, and the two visited frequently in the two years Thoreau lived on Walden Pond.

I recommend starting early in the morning at Walden Pond, visiting the cabin site before the crowds pick up, then starting the Emerson-Thoreau Amble from Thoreau’s front door (or where his front door would have been). The trail isn’t as clearly marked as it could be while inside Walden Pond State Reservation, and you will need to cross an intersection to pick up the Amble again. But once you do, the trail is well-blazed and this detailed guide explains each natural landmark along the way.

Once on trail, you’ll pass through meadows, swampland, and by a lake, and you can expect to see wildlife and public art installations along the way. The trail ends next to the Concord Independent Battery Gun House (Concord has a significant Revolutionary War history). Take a right and you’ll see Emerson’s white 1832 home. Also within walking distance: Louisa May Alcott’s Orchard House, The Wayside (also known as “The Author’s Home,” as Hawthorne, Emerson, Thoreau, and Margaret Sidney all lived there), and Sleepy Hollow Cemetery, where Concord’s most famous writers are all buried together on Author’s Ridge.

If you get an early enough start at Walden Pond, and plan your tour times perfectly, you could explore all these sites in one day. We explored this section of Concord entirely on foot, which felt appropriate to the authors we were paying homage to, and walking allowed us to slow down and enjoy Concord’s scenery. It’s remained mostly unchanged since the 1850s so don’t be surprised if you feel like you’re walking in Louisa’s footsteps, daydreaming along Thoreau’s paths, and contemplating Emerson’s nature.

–> Read this post to plan your own literary trip to Concord

I visited over 20 literary landmarks on my literary road trip, and the hikes were among my favorite stops. You can learn a lot about an author’s life by walking through their home, and you can learn just as much by meandering through the woods that inspired their stories.

–> Check out Ashley’s full route on Roadtrippers

Literary New England Pilgrimage on Roadtrippers

Ashley has loved books since before she could read, and travel since her first trip to Washington, D.C. in the 5th grade. You can find her buying more books than she could ever read, and planning more road trips than she can ever take (and eating too many Reese’s Pieces, but that seems unrelated). You can follow her on Instagram @bigworld_books (check out the Highlights for all her literary road trip stories!). 

Let’s Talk!

I’d take this trip all over again, and would love to hear your recommendations for other literary nature sites I should add to my list! Leave your suggestions in the comments below!

Have you taken a literary inspired trip? Would you like to guest post? Drop me a note!!

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