The Tour de Olmsted

A road trip through the OG landscape architect's parks

If you’re reading this particular newsletter, that means that you haven’t succumbed to the wretched humidity that transformed New England into a pressure cooker in early July. Congratulations, but also, to quote Geena Davis in The Fly, “Be afraid. Be VERY afraid.” Because we still have at least one month of stickiness left. And that’s why I’d imagine several of you might be putting your hiking plans on the backburner for the near future. So this week, I want to offer you another idea for an adventure involving open green space; a journey that oscillates between naturalistic and air-conditioned.

I want to tell you about the Tour de Olmsted.

For those of you who found your way to Mind The Moss more recently, I’ve written a lot about Frederick Law Olmsted: the ingenious landscape architect who pretty much created urban parks as we know them. Central Park was Olmsted’s first serious foray into landscape architecture, after spending several years working as a journalist in the Antebellum South. In his spare time, Olmsted had paid a few visits to England, where he experienced public gardens for the first time. This blooming exposure to what you could do with greenery in a cityscape had a profound effect on Olmsted’s designs. He saw public parks as “the lungs” of industrialized cities that were horrifically polluted, but also as a place where people of all walks could come together and see each other crossing paths—a timely idea, given that Central Park was created during the Civil War.

But as most Olmsted historians have said, (the dude was so prolific that he has his own subgenre of historians!) Central Park was just the beginning. Olmsted and his business partner, Calvert Vaux were overwhelmed with commissions from public and private clients, looking to replicate the magic of Central Park on their own turf. When you look at all the parks, college campuses, and estates of the northeast, the region appears to be covered with Olmsted’s fingerprints. In fact, the prestige of having an Olmsted work in your domain is so staggering that some green spaces have been incorrectly attributed to Olmsted. And on the Tour de Olmsted—a three day road trip through some of Olmsted’s most gorgeus parks in New England—you’ll get to visit one of these Olmsted forgeries, along with the authentic Olmstedian wonderlands!

Because we’ve got a lot of ground to cover here, we’re going to segue from narrative structure to something resembling more of an itinerary. But let me say a few things from the top. I took this mini-road trip in late summer of 2021, and it was one of the most sumptuous long weekends I’ve had since the onset of the pandemic. The parks, green spaces, and woodlands featured on the Tour de Olmsted are the backbone of the agenda. You’ll have plenty of opportunities to fill in the gaps when it comes to food, drink, lodging, and the specific roads you take to reach each Olmstedian site. But to get you pointed in the right direction, I’ve included a few of my own choices.

Now that we’ve gotten that out of the way, grab your broadest-brimmed hat, lace up your hiking shoes, and an extra grab large iced coffee. The Tour is about to kick off.

DAY 1: NEW YORK

New England purists can skip Day 1 if they wish, but any Olmsted tour in the northeast needs to start with the place where America’s urban parks were born. New York was Olmsted’s laboratory. This partially explains why the city now has hundreds of green spaces that come in more shapes and sizes than all the creatures in Pokémon ball.

Morning: Take the MTA Metro North train to New York from the Stamford, Connecticut Transportation Center. The onsite garage at the Stamford station offers parking for a bargain $10/night. If you’re beginning your road trip on a weekday, get here as early as you can. Ideally before 7:30am. A backup option is the West Haven station lot. It’s only $6/day, but parking here will mean a little more driving on Day 2 of the road trip.

Late morning/early afternoon: Drop off your bag at the front desk of your hotel or at a pay-by-the-hour luggage locker, grab some savory takeout, and begin with a traverse of Central Park. As famous as Central Park is, only a handful of people ever bother to walk south to north across the entire 2.5-mile expanse. This is a neat way to discover the lesser-known oddities in the park, like The Loch: a pond on the quieter north side that feeds roaring cascades and a stream which leads you under an arched bridge, into the most scraggly forest found within the park. (It’s a great birdwatching venue.)

Late afternoon/evening: Recover from your Central traverse at your lodgings, or at a local dive bar with happy hour specials, and then hop onto the subway and take it to Brooklyn. Get off at 15th Street-Prospect Park station, and enter Prospect Park, the titanic sequel to Manhattan’s signature green space. Be sure to check out The Ravine, which is the home of Brooklyn’s last remaining forest and reliably cool. And consider making your way past Prospect Park Lake before scavenging for your dinner nearby.

DAY 2: NEW YORK TO NORTHAMPTON

Morning: After breakfast, catch the MTA Metro-North train back to the station where you left your car and set the controls for Bridgeport’s Seaside Park. Gawk at the giant stone archway at the entrance and share the waterfront path with the fishermen. Then, hop back into your jalopy and head north for Hartford, where you’ll visit The Institute of Living. One of the first psychiatric facilities in America, the institute’s earliest brass were intrigued by the theory that green space could have a thereapeutic effect on the mind. Olmsted was hired to create onsite gardens where patients and visitors could immerse themselves in flora. Today, you can enter those gardens via Retreat Avenue.

Early afternoon: Linger in Hartford for a bite to eat (I enjoyed the carne asada plate at Monte Alban Restaurant) and continue north over the line to South Hadley, MA. Here you’ll discover the prodigious woods and waters that are part of the Mount Holyoke College campus. Olmsted tinkered with the early designs for the campus and his two sons, who took over the family business in the early 20th Century, completed the project. Be sure to lounge in the grass by the roaring dam waterfall on Upper Lake.

Evening: Motor down the mount into Northampton, enjoy a sunset dinner from one of many esteemed restaurants (you can never go wrong with the takeout summer pizzas from Hungry Ghost Bread) and when you’re finished, take a stroll around the campus of Smith College; another Olmstedian conquest in the world of academia. Then, head to your lodgings and get a good night’s sleep, as Day 3 is the biggest day of the tour. The sound of the dam cascade at Hatfield’s Old Mill Inn is a rather effective sedative.

DAY 3: NORTHAMPTON TO BOSTON

Morning: The final day of the Tour de Olmsted is a tale of two Massaschusetts cities. Both feature bounteous parks, but only one of them is a genuine Olmsted work. First, make your way to Springfield and enter the grand corridor of trees at Forest Park: an enchanting expanse of urban forestry, lily ponds, ornate bridges, and curiosities like rock slabs that contain preserved dinosaur footprints. For decades, Forest Park was attributed to Olmsted, but a handful of historians did some recent archival digging and discovered that the man who designed this park was an architect named Justin Sackett. How does a mistake like this happen? How does it endure? Could having an alleged Olmsted park boost local property values? Chew on this as you poke around.

Late morning/early afternoon: Enter the cacophony of the Mass. Pike and drive east, with a stopover in Worcester for lunch. Here you can bag a bonus Olmstedian work: Elm Park, which features a beautiful pond and an arched bridge over the water that’s surprisingly angular and steep. Just like the Mount Holyoke campus, this park was designed by Olmsted’s sons and not the OG himself. (But you don’t have to share this when telling people about your Tour de Olmsted.) Here, I devoured a bowl of chowder from The Sole Proprietor, which is a 10-minute walk from the park’s north perimeter.

Afternoon/evening: Continue west to Boston, and park on Williams Street in Jamaica Plain. Or any of the nearby residential streets. At the east end of Williams Street, you’ll find an entrance to Franklin Park. This juggernaut of a park connects Jamaica Plain with Dorchester and Roxbury, and as you follow a bubbling stream into the park, you’ll soon hit a junction. To your left, a winding staircase disappears into “The Wilderness”: the park’s most thoroughly forested section, through which can wander to visit White Stadium and old rusting bear cages from an earlier incarnation of Franklin Park Zoo. To your right, a stone archway offers passage to Scarboro Pond, the park’s crown jewel water body, and the William J. Devine Golf Course. You can follow one of these paths from Point A to B, or undertake a loop hike around the park. Both are winners.

But the totality of Franklin Park isn’t the only reason why the Tour de Olmsted ends here. Franklin Park also happens to be the south end of the Emerald Necklace: an epic linear park system that Olmsted spent the last decades of his life designing from Brookline, where he eventually settled down so that he could preside over his baby. The “Necklace” is a near-unbroken chain of green spaces that extends from Franklin Park to Boston Public Garden and Boston Common. To walk the whole thing is an unforgettable city hike of roughly 7-8 miles, depending on how many side trails you explore in featured spaces like Arnold Arboretum, Jamaica Pond, and The Fens.

By now, at the end of your tour, you’ll either never want to hear the name “Olmsted” again, or you will have discovered an insatiable appetite for anything connected to the man, myth, and legend. IIf you find yourself in the latter position, consider extending your tour with a full-blown Emerald Necklace traverse. You might as well. There are no Olmsted gift stores anywhere along the tour route where you can buy t-shirts or a beer coozy bearing Olmsted’s likeness. (There really should be a store where you can buy swag like this.) But his most ambitious project still flourishes in Boston, and when you’ve finished your traverse, you can stop by his preserved homestead in Brookline.

Got any questions? Concerns? Olmsted parks that I missed? Drop me a line anytime. And if you undertake the Tour de Olmsted this year, please let me know how it goes!