Perfect Day Trip to Millerton, NY; Hikes, Cafes, & More!

Spend the perfect day in Millerton, NY, where adventure, charm, great food, and shops await! We’ll explore scenic hikes, walks, bike paths, where to eat, and what to do in Millerton!

From hikes up Alander Mountain to easy flat walks at a land trust to Harney & Sons Tea Shop and the BEST antique store I’ve been to in a while – you’ll create the perfect day using this guide to Millerton NY.

Right over the border of Salisbury CT, Millerton is often the perfect escape and day trip for us. And no matter how often I’ve been, I always get excited when we come upon its downtown and the main hub.

Whether approaching from any of the cardinal directions, one knows when they’ve officially rolled into Millerton, New York. A gently curving main street is the lynchpin connecting a cozy old northeast back roads network.

Your head, lolling out the window or your car reflects off the window panes of a brotherly array of local businesses as you wind through town.

Founded in 1891 and came together as a railroad hub in upstate New York, the energy and vibe here is still one of exploration and adventure.

When looking at the patrons and passersby of the town, you get the sense that everyone is either getting suited up and ready for some outdoor excursion, or is just returning from one and looking to put up their heels.

With the Taconic and Catskill Mountain ranges a stone’s throw north and west, Millerton is a perfect place to get an early morning breakfast before hitting any number of local trails.

But where would I get some delicious baked goods and specialty coffee drinks in Millerton, you ask?

Adventurous Day Trip Itinerary for Millerton, NY

1st Stop: Cafes in Millerton ☕️🥐🥙

Irving Farm

Right on Main Street Irving Farm is usually my first stop in town. A hip coffee shop that roasts their beans at the factory further down the road in Millerton, you’ll love their lattes, baked goods, and sandwiches.

A welcoming, comfortable environment greets visitors with ample seating and a homey atmosphere.

Couple a perfectly brewed cup-o-joe or any of a variety of assorted specialty drinks with a tasty fresh baked good or classic bacon, egg, and cheese and you can be off to the day’s races happily satiated and well caffeinated.

🚗 44 Main Street, Millerton

Harney & Sons Fine Teas

A rustic tea room with an extensive choice of world-class blends, plus sandwiches, soups & a terrace.

As someone who LOVES tea, I always stop at Harney & Sons when visiting Millerton. The tea shop has a whole wall of tea, over 250 varieties. If you like black tea – good luck. There will be way too many to choose from and you’ll love every minute of reading all their names and determining the differences.

Not a tea person but know someone who is? Definitely stop here. There are so many gifts and unique home items from an array of honeys to stationary and special pens!

In addition to the tea shop there’s also a cafe and outdoor terrace where you can order tea, coffee, breakfast, soup, or lunch. I often stop here after a hike in Millerton to refuel with a baked good (love their salted dark chocolate chip cookie) and grab some tea for the road.

🚗 13 Main St, Millerton

With the morning fuel up covered let’s go hit the trails in Millerton!

2nd Stop: Hikes in & Around Millerton

🥾 Iron Mine Pond Loop: 4.7 miles and 698 feet of elevation gain, Moderate

🔗 AllTrails link and 🚗 Click to navigate to parking at 41.9675, -73.4975 off Shagroy Rd.

The trailhead for this fantastic little trek can be found just outside of downtown Millerton off of Shagroy Road. There is more than meets the eye as you make your way into the overgrowth from the parking area.

You’ll walk through a dense tunnel of luscious greenery (in the summer months at least) for about .2 miles until abruptly entering a beautifully landscaped wide open field.

From here you’ll traverse the steep banks of an old iron mine that has filled its depths with fresh water from surrounding tributaries to create an epically stunning pond. There is a little beach area (we had it all to ourselves!) where you can soak up some peace, the only sounds being the wind through the leaves and the gentle flow of a freshwater brook.

Continuing on you’ll follow an old logging road, rutted and stony but easily walkable, through several varying forest scenes.

At about the 1.5-mile mark (following the loop counterclockwise), you’ll reach a junction and take a right to stay on the South Taconic Trail. From this point, in just over 0.5 miles you’ll stumble out into a rocky clearing revealing superb views to the north and west.

From this vantage point you can marvel at the slow goings on of the working farms far below your feet as well as Alander Mountain to the north and the Catskill Mountains to the west.

🌟 Be sure to head on the little trail just to the left of the first lookout for another and even better wide-open view.

Follow the South Taconic Trail back for another 0.5 miles until taking a right onto the Rudd Pond-Trail. This section of trail will bring you gently through the Rudd Pond area of Taconic State Park and back to your waiting vehicle.

🥾 The Kite Hill Loop, Overmountain Conservation Area: 3.2 miles and 357 feet in elevation gain, Easy

🔗 AllTrails link and 🚗 Click to navigate to parking at 42.02282, -73.53771 off Catalinas Rd.

This land preserve is spectacular. I can’t say it enough. I felt like I was walking in the hills of England or Ireland here.

A true hidden gem just outside of Millerton along the western voyage towards the looming Catskill Mountains.

This loop begins after parking off of Catalinas Road and heads in a counterclockwise rotation (or you can walk clockwise to get to the Kite Hill Gazebo view faster! Do this if short on time).

Having already been elevated via the drive to this hike you’ll enjoy majestic vista views during virtually every waking second while walking.

Enjoy a leisurely stroll on this trail that intersects multiple colonial farm fields, separated by old field stone walls and rustic wooden fences all while enjoying stunning looks at the Riga Plateau of Massachusetts and Connecticut.

After about 2.8 miles of breathtaking scenery you’ll come across the Kite Hill Gazebo…and here you will be stunned to a stand still.

From Kite Hill Gazebo a visitor will be floored by one of the hands-down most spectacular views of the Catskills Mountain range! Layers upon layers of hills stack upon one another until finally meeting the great wall of the Catskills.

Once you can peel yourself away from this amazingly special vista simply follow the trail downhill for the remaining .5 miles to your vehicle.

🚲🥾Harlem Valley Rail Trail

Don’t like to hike?! How about a paved walk or bike ride?!

Travel up to 26 miles (one way!) on the well-known Harlem Valley Rail Trail on foot or on wheels. This is a great family walk to do in Millerton for those not into walking on dirt and rocks. 🙂

Park at Harney & Sons tea shop to access a great starting point for this trial right in downtown Millerton.

🥾 Alander Mountain, 4.4 miles and 1,528 ft elevation gain, Hard

🔗 AllTrails link and 🚗 Click to navigate to parking on Undermountain Rd.

Ok friends, I had to have a true hike on this list – one that really gets your heart pumping and leads to those big mountain views. ⛰

Do you feel ready for a challenge?! Only take this one on if you do!

Alander Mountain via the South Taconic Trail is accessed from a parking lot and pull offs along Undermountain Rd just outside Millerton in Copake, NY.

You’ll get a one mile mostly flat warm up before you ascend and trust me, you’ll want to take a few breaks along the way on the way up.

But the top of Alander Mountain is a true wide-open mountain summit with almost 360-degree views.

Now that you’re tired (tired on a beautiful level only achieved after a long time spent in the great outdoors!) it’s time again for FOOD!

3rd Stop: Lunch/Dinner in Millerton

Oakhurst Diner

You can’t drive down Main Street in Millerton without jealously looking at the happy patrons of this classic 50s-style diner enjoying their delicious eats outside on the shady patio. And when you’re done with your hike you definitely want to be one of those people!

This place is very deservedly popular, with an eclectic menu and jovial atmosphere. With an Asiatic spin on traditional American, any pallet can find something to satiate themselves in fine fashion at Oakhurst Diner.

Enjoy your meal as you observe the passing foot traffic of other like-minded adventures AND Oakhurst Diner is dog-friendly so hang on to your pup while you sit outside while you eat.

I love this place because it truly is at the center of what makes this town great: it’s tightly knit and familial nature.

Taro’s

Taro’s is a no frills, yet fantastic Italian eatery.

They have grinders (a.k.a.: heroes, subs, hoagies, etc.), pizza, wings, and salads down to an absolute science.

This family run and welcoming establishment is all you’d need for a re-fuel following a strenuous morning or afternoon.

Avocado Cafe

Fantastic traditional Mexican.

I’m tempted to simply leave it at that but I’ll do the Avocado a bit more justice in saying that if you’re looking for some real deal Mexican for lunch or dinner, there is no place better.

Fresh as the day is long, and prepared with love and care, pick anything at random off this stacked menu and you won’t be disappointed.

Ice Cream: Candy-O’s Sweet Shop

Walking into this colorful shop is to be transported into a cheerfully younger of yourself.

All senses spring to life as you gaze up down the array of candies and sweet treats, all in the fragrant air of freshly baked waffle cones.

With charming, vintage decor, Candy-O’s offers up an astonishing assortment of not just  abundant selections of chocolates and candies, but ice cream as well.

Treat your six-year-old self and the entire fam to a much-deserved what-ever-the-heck-they want from Candy O’s to top off your day in Millerton!

🛍Shopping in Millerton

One of my favorite places to stop when visiting Millerton has become this antique store – Old Mill of Irondale located right outside of the main downtown area located at 6082 NY-22 in Millerton.

I am usually just a browser when it comes to antique stores but this place had unique plus fairly priced items. I walked away with the cutest mini salt + pepper shakers and an antique plate with a picture of the White Mountains in New Hampshire. Go see what you find!

There’s a whole cluster of super cute shops along Main Street in Millerton. Some of my favorites include Oblong Books, demistasse (a gift shop), and Millerton Antique Center. Stroll in and out of these fun shops!

I hope you enjoyed this Millerton day trip itinerary featuring the best hikes and food in town!

This is truly one of my favorite day trips from Connecticut and where I go when looking for great food and adventure!

From the numerous hikes and trails to choose from around Millerton to the tea shop and downtown diner and fun stores to pop into – I never get sick of it and love seeing the village of Millerton in every season.

Let me know if you go and enjoy your time there!

Happy trails 💗🐶🥾

Looking for more fun and beautiful day trips in New York that aren’t too far from Connecticut?! ⬇️⬇️

FAQs about visiting Millerton