13 New York Towns With Unforgettable Main Streets
In the small towns and villages around the state of New York, there are main streets that can sweep you away. In Sleepy Hollow, you can follow the flight of poor Ichabod Crane (and the Headless Horseman in hot pursuit). In Tarrytown, you can hear some of the best live musicians in the world in incredibly intimate venues. In Cold Spring, you can have (what's said to be) the best ice cream in the world. Some of these main streets offer views of natural wonders, while others lead to Gothic mansions, but from all of these New York main streets, you will find wonders you cannot forget.
Greenport
Greenport’s Main Street is the heart of the Greenport Village Historic District, a dense collection of beautifully preserved whaling captains' homes, museums, and commercial buildings from the 18th to early 20th century. This is a wonderful place to lose yourself in over 200 years of maritime and architectural history. To take a self-guided walking tour, begin by picking up a map and starting out from the Ireland House (319 Main Street, circa 1750s). Previously, this was home to many working families and is now home to the Stirling Historical Society (the experts on the district).
At the foot of Main Street, you will find the completely delightful Mitchell Park & Marina. You can't miss the iconic Antique Carousel, which is over 100 years old and still features its traditional brass ring grab. And just steps away from the merry-go-round, you will find a hodgepodge of beautiful old-timey entertainments, including a camera obscura, and the 1870s replica of a village blacksmith shop that hosts live forging demonstrations.
Sleepy Hollow
When you walk through the streets of Sleepy Hollow, you are walking through the setting of a legendary tale. The main street, Beekman Avenue, is celebrated to this day for its quaint storefronts. But it’s the connection to Washington Irving's short story (that's never been out of print since it was first published in 1820) that really makes visitors... lose their heads. Readers may remember that the schoolmaster, Ichabod Crane, began his famous flight from the headless horseman at the home of the Van Tassel family.
If you follow the flight of poor Ichabod Crane, you will find an 18-foot Headless Horseman Statue along Route 9. According to the Visit Sleepy Hollow website, this is one of the most visited sites in town. And it's located just a few feet away from the Bridge where Ichabod very nearly escaped the horseman. Or at least, it's the best guess by historians of which bridge must have been described by Washington Irving because this one leads to the Old Dutch Church and its burying ground. The church, which is associated with the Headless Horseman legend, is nearby and dates to 1685, with the congregation beginning in 1697. This is still the home to an active congregation, so while visitors are always welcome, it's requested that everyone be respectful of services. And remember, if you find yourself near the churchyard in the wee hours of the morning, be sure to be on your guard, because the headless horseman will be "in a hurry to get back to the churchyard before daybreak.”
Narrowsburg
Set in the Catskills, the main street of Narrowsburg packs big city sophistication into a small hamlet of charming 19th-century buildings and highly browsable shops. Take, for instance, One Grand Books. You won't find a standard bestseller section here. The entire store's inventory is organized exclusively around the top 10 "desert island" book picks from celebrated thinkers, writers, artists, and other creative minds. According to The New York Times, this bookshop is “everything that Amazon is not - [a] modern, yet intimate, 550-square-foot space perched above the Delaware River, with a beautiful view of the water."
Next, explore the oddities at Maison Bergogne. This former 1920s industrial space operates less like a standard antique store and more like a moody, museum-caliber showroom. Curated by the French artist, Juliette Hermant, the shop sells architectural salvage from local Catskill barns and whimsical vintage oddities.
And while you are in Narrowsburg, you should absolutely get a view of the "Big Eddy" from the Observation Deck on Main Street. The "Big Eddy" is the deepest point of the Delaware River (113 feet deep here, much deeper than the river's average depth of 4 to 5 feet), and it is also the narrowest point along the river (only 200 feet across and flanked by a rocky geological formation). This is the reason why the settlement here was originally called "Narrowsburg." From the charming wooden Observation Deck, you can sometimes see the eddy in a state of calm, sometimes with a visible whirlpool, and always in a state of natural beauty.
Cold Spring
The Main Street of Cold Spring slopes down along the banks of the Hudson River and is said to be one of the best-preserved 19th-century townscapes in the region. Cold Spring’s Main Street feels like a step back in time, pairing its historic charm with plenty of places to shop and eat. Architecture lovers will find much to admire in the village’s well-preserved Colonial and Victorian buildings, while the surrounding side streets reveal quiet gardens, handsome old homes, and the small details that make the village feel so carefully preserved.
If you have got shopping for presents to do, you should know that the Cold Spring Main Street is famous for its vintage and antique shops. Check out the Cold Spring Antiques Center, where 27 different dealers are selling vintage clothes, jewelry, records, memorabilia, and all manner of oddities out of a 19th-century bank. You will also want to do some shopping in the Cold Spring General Store. Here you will find locally sourced handmade goods from artisans living and working throughout the Hudson Valley and New York.
After all that window shopping, you will want to grab a bite in one of the many highly rated restaurants that are on and around Main Street, but no matter where you get your lunch or dinner, be sure to stop by Moo Moo's Creamery. This cute little ice cream shop is a wildly popular place to get a scoop (or two or three). The shop only serves homemade ice cream and continually experiments with flavors. It is said to be some of the best ice cream in the world. There is one way to find out for yourself, so be sure to treat yourself here after a fabulous day of shopping on the Main Street of Cold Spring.
Skaneateles
Often called the mini-Hamptons of Upstate New York, Skaneateles is considered to be the "Jewel of the Finger Lakes." The Main Street here is both highly walkable and historical, filled with the storefronts of boutiques and cafes that have been looking out onto the clear waters of Skaneateles Lake since as early as 1796.
A favorite spot to start a walk down the main drag of Skaneateles is Clift Park, situated right in the heart of town. This is a small but very thoughtfully made park. A walkway lined with benches follows the shore in such a way that almost anywhere you sit, you will have a breathtaking view before you. That said, the pier at Clift Park is still considered the very best vantage point to take in both the view of the village and the water (which shifts from emerald to deep sapphire hues and can seem to go on forever).
Right across from the park, there is a favorite place for weekenders to stay. The Sherwood Inn was established in 1807 as a tavern built for Isaac Sherwood’s stagecoach business, and it still offers lodging and dining in the heart of Skaneateles.
It's no surprise such a stunning locale has attracted artists for many years. To soak in some culture, visit Skaneateles Artisans, a charming gallery located in the historic "Old Stone Mill." This gallery features the work of a hundred or so local artists and artisans across a wide range of mediums. The venue is dedicated to stimulating the town's culture and economy by making works available for sale, so be sure to take a stroll through the shows and see if anything captures your fancy.
Lake Placid
Welcome to the gorgeous and lively Main Street of Lake Placid. This is a place made of many delights. You can easily spend an afternoon window shopping in funky little artisan shops for everything from a stylish hat for your head to a "sanctuary" for your feet. One of the newest spots to open on Main Street is Faizy’s Fun House Arcade, where you can play skee-ball, basketball, plink, and much more. Another favorite place to stop and play is at Big Z’s at Lake Placid Lanes, which offers bowling lanes, arcade games, a casual restaurant, and a full bar. After a big day of shopping and playing, why not go to a cool vintage theatre and catch a movie at The Palace Theater? This has been a treasured landmark on Main Street since it first opened in 1926, and to this day, stepping inside the lobby from under the stylish marquee is like stepping into the glamour of early Hollywood. Of note, the theatre organ here is the only one in New York that's been preserved with its original installation (apart from the one in Radio City Music Hall). When you get there, you will see for yourself why The Palace was given a "Very Special Place" North County Heritage Award. In short, the Main Street of Lake Placid is anything but "placid." It offers a tremendous amount of unforgettable fun.
East Aurora
The village of East Aurora is where America’s "Arts and Crafts movement" (aka the "Roycroft movement") began over a century ago, inspiring American architecture and design in the early 20th century and continuing to exert a creative influence to this day. In keeping with a world-class eye for design, the Main Street here features a red-brick pavement as it did almost 100 years ago, with street lights that look like gas lamps. And the village boasts two National Landmarks:
The Roycroft Campus was the center of the Arts and Crafts Movement during the turn of the century. Visitors can tour the campus (be sure to check seasonal hours for tours) and see rare artifacts and learn more about the people, products, and philosophy that inspired the Arts & Crafts Movement. The Roycroft Campus gained National Landmark status in 1986. If you are interested in learning (and shopping) for more Roycroft artistry, you should also stop by the Elbert Hubbard Roycroft Museum, which features an extensive collection of Roycroft arts, crafts, and books about the Roycroft movement.
If this isn't enough cultural history to enjoy in one small town, don't forget to visit the second National Landmark in East Aurora: the President Millard Fillmore Home. Built in 1826 by Millard Fillmore for his bride, Abigail, this restored historic cottage has been furnished in keeping with its original era. With so much to do here (not even mentioning vintage shops, local breweries, and the Knox Farm State Park), you can see why visitors often spend at least a weekend here.
Watkins Glen
This town is renowned for wine, waterfalls, and motorcar racing. The Main Street here is (Franklin Street), which runs along Seneca Lake, and provides easy access to all the things for which Watkins Glen is famous.
To begin with, Watkins Glen is in the heart of Finger Lakes wine country, so you can find several local wineries and craft beverage tasting rooms here without leaving town, or you can plan a more extensive tour through the wineries and 20+ surrounding vineyards along the Seneca Lake Wine Trail. A recommended stop (on Franklin Street) on the official wine trail is Seneca Harbor Station, with its waterfront dining room and outdoor beach seating.
As for waterfalls, the main entrance to Watkins Glen State Park is located right off Main Street. This spectacular 2-mile Gorge Trail will take you past 19 waterfalls, beautiful stone bridges, and 800 stone steps carved directly into a 200-foot-high cliff.
New Paltz
New Paltz is a famous destination for mountain climbers worldwide. Shawangunk Ridge offers a host of trail options for hikers and bicyclists, and "The Gunks" are one of the busiest places for rock climbing in North America. But Main Street in New Paltz is also a vibrant place with a storied history, college-town energy, and a penchant for indie shops.
Main Street is famous for its independent retailers and bookstores like Barner Books, which specializes in out-of-print books and also offers a wide selection of handmade journals.
And for even more shopping, just steps off of Main Street, go explore the Water Street Market, which is an open-air "European style" shopping village that is packed with indie boutiques, a two-story antiques barn, art galleries, and cafes.
Then you can step back in time along Historic Huguenot Street. This National Historic Landmark District features seven unique stone houses dating to the early 1700s, a burial ground, and a reconstructed 1717 stone church, all in their original setting.
Saranac Lake
Saranac Lake's Main Street is surrounded by scenic mountains and lakes, and art is everywhere. For a whirling experience of the local charm, hop aboard the Adirondack Carousel, a true treasure of the town, where every animal has been hand-carved (and every animal can be found in the Adirondacks, like moose, trout, bears, and loons).
This is just the beginning of Saranac Lake's celebration of arts and imagination. There are many times, especially in the summer, when art takes to the streets in a series of festivals and "Third Thursdays." But if music is more your scene, be sure to stop by the Waterhole, a great bar open every day that hosts live music and parties almost every week.
You will also want to spend a little time in the Hotel Saranac, a beautiful building that takes you back to the roaring twenties. Today, there is an almost intimidatingly tempting gift shop, a spa, a restaurant, and even ghosts.
Cooperstown
Main Street in Cooperstown is just two blocks long, contains the only traffic light in the whole village, and yet this is where you will find unique shopping and memorabilia shops, delectable dining, and, oh yes, the National Baseball Hall of Fame and Museum! To quote the Hall of Fame's website, this is "the mothership. Three floors of baseball history, jaw-dropping artifacts, and interactive exhibits that make you forget you've been inside a museum for three hours."
Baseball is a major presence in this town, and for good reason. Visit Doubleday Field here, an historic 9,791-seat baseball stadium that is just steps from the Hall of Fame, because when you are there, you are on hallowed ground. According to a myth, Civil War General Abner Doubleday invented baseball on that very spot in 1839.
Now, why not round out the day at the Doubleday Cafe, where they serve the best burgers in town (and don't forget the homemade desserts). All this and much more can be found along just those two blocks of Main Street in Cooperstown, New York.
Tarrytown
Tarrytown is just a few miles from Sleepy Hollow, which shares some of that town's legendary fame. And while the streets of Tarrytown are perhaps their most spooktacular during Halloween, its Main Street is completely charming by its own right and has been voted "Best Main Street in Westchester" three years in a row by Westchester Magazine.
Consider the Tarrytown Music Hall, which is listed on the National Register of Historic Places because it's the 5th-oldest in New York (older than Carnegie Hall) and one of the oldest music halls in the nation. To this day, it books national musical and comedic acts, offering a packed lineup year-round.
There is also the Jazz Forum Arts bringing world-class live jazz musicians into an intimate 90-seat performance venue sometimes called a "living room." There is no elevated stage, so the performers are truly in the same space as the audience. Naturally, there is a full bar, and between sets, there is a lounge where every piece of furniture tells a story, including a pool table for patrons to enjoy. This is considered one of New York's premier jazz clubs and is not to be missed.
Ready for even more culture? Then you must visit Lyndhurst, one of America’s finest Gothic Revival mansions. Lyndhurst was designed in 1838 by Alexander Jackson Davis. Its architectural brilliance is complemented by its comprehensive collection of original decorative arts and the estate’s park-like landscape.
Beacon
Another favorite Main Street is the former factory town of Beacon, now a bastion of indie arts, craft brews, and top-tier eats.
There are artsy endeavors all along Main Street, but do not forget the Howland Cultural Center. This nonprofit (run entirely by volunteers) is considered the 'Jewel of Beacon’ for fostering art, culture, and history. They preserve and operate out of the historic 1872 Richard Morris Hunt building, originally designed as the Howland Circulating Library. Today, they not only host art exhibitions but also host an eclectic array of events that elevate and celebrate art across mediums.
For brews, a favorite spot is the Hudson Valley Brewery right on Main Street. This is a place where craft beer connoisseurs can truly appreciate the time and care that goes into making the 100% New York State beers served here (and wines and ciders).
For eats, again, there are almost too many places along the one-mile Main Street to choose from, but consider Dave the Butcher, which is located less than a hundred yards from the weekly Beacon Farmer’s Market. This eatery features elegant backyard seating and "the best produce and meats sourced from as close to our front door as possible." Almost everything comes from the Hudson Valley region, so naturally, the menu changes from week to week, but you can always count on something truly first-rate here at Dave the Butcher (much more than just a butcher).
Swept Away by New York Main Streets
It's so New York to take a small space, say just a few blocks or a mile of Main Street, and make such spectacular statements. From the world-class live music at Tarrytown, to the wine and waterfalls of Watkins Glen, to the home of the Roycroft movement in East Aurora, to the home of baseball in Cooperstown, there is something for everyone to enjoy on these small town main streets with so much savoir faire.
