Blake Walsh

20 Best Things to Do in Callicoon, NY

  • Published 2023/03/29

In Sullivan County, you’ll find one of the oldest towns in the foothills of the Catskill Mountains, also known as Callicoon.

This small town is located on the edge of New York, right next to the Pennsylvania border.

On your visit, you’ll find a tourist hotspot with an appealing historic vibe and many sightseeing attractions.

Callicoon is often split into Upper Main Street and Lower Main Street, which you are free to explore if you want to experience everything in the town.

Its location next to the Delaware River makes it a great vacation spot packed with various water activities.

Here are the best things to do in the charming town of Callicoon, NY:

Visit Callicoon’s Historic Western Hotel

Exterior of The Western Hotel

John Arehart /

The Western Hotel is one of Callicoon’s most famous landmarks with its 1852 Victorian design.

The National Register of Historic Places has recognized the hotel’s historical and cultural significance in Sullivan County.

This crown jewel is still fully operating today.

Drop by and see how it has served this community since its establishment.

View of The Western Hotel from across the street

Vpuliva, CC BY-SA 3.0, via Wikimedia Commons

Its indoor decor gives you a mix of a modern-day vibe with an elegant vintage charm to remind you of its rich past.

You can dine at their restaurant, which features an original, well-preserved mahogany Bar Room.

Play a round of pool on their billiards table, or keep warm by their fireplace.

The Western Hotel provides a one-of-a-kind experience.

Try and add this place to your itinerary while visiting Callicoon.

Facade of the Western Hotel

Jaclyn Vernace /

Stop by Rafter’s Tavern

Rafter’s Tavern is a restaurant, art gallery, and music venue in one.

Whether you’re looking for a place to grab lunch or dinner, listen and tap your foot along to music, or admire some lovely and unique artwork, Rafter’s Tavern is the place for you.

Gather your friends and family and enjoy this tavern’s cozy ambiance while indulging in some delicious food and drinks.

You can also rewind and relax as you listen to the live music in the tavern.

Grab a cocktail, eat lunch, or stroll through their gallery for a fun and exciting experience.

Rafter’s Tavern is only open from Thursdays to Sundays, so plan accordingly.

Play a Round of Golf at the Golf Club House Villa Roma Resort

This fully operating resort in Callicoon also has one of the best golf courses in the town.

It’s perfect for a friendly round or two with your friends.

Found on the eastern end of Callicoon, the Golf Club House Villa Roma Resort offers an 18-hole course that caters to golfers of all skill levels.

You also have the option of a golfing package.

Whether picking up a golf club for the first time or a seasoned player, you can drop by this course and enjoy the cool breeze, stunning views, and high-quality fairways.

They also have a nearby bar and restaurant where you can grab a refreshing drink or a light meal to keep you going.

The Golf Club House Villa Roma Resort is family-owned and has operated since 1969.

See a Show at the Callicoon Theater

Exterior of The Callicoon Theater

Alizada Studios /

The Callicoon Theater is situated at the heart of Callicoon and is one of the oldest buildings in town.

Established in 1948, the oldest-running theater in Callicoon continues to attract first-time visitors.

They drop by to see the historical value of this vintage theater.

With a 350-seat capacity, the Callicoon Theater shows a variety of films ranging from old indie films to the latest blockbusters.

Marquee of The Callicoon Theater

John Arehart /

The theater also hosts concerts, throwback events, and more, providing a wide range of entertainment for you.

Its indoor decor takes you back to the late 1900s, back when they initially built this cinema.

Despite being a historic establishment, the Callicoon Theater ensures a high-quality experience.

The theater comes equipped with cutting-edge modern technology, surround sound, and comfortable seating.

Don’t forget to grab your popcorn and snacks at their concession stand before taking your seat.

Front view of the Callicoon Theater

Rabbitti /

Grab a Slice of Callicoon’s Best Pizza at Peppino’s Family

Often shortened to “Peppino’s,” Peppino’s Family is a favorite local diner that serves Italian cuisine.

Serving the community since 2007, this eatery in Callicoon is the oldest pizzeria in town.

Its iconic recipes have earned them a loyal following from locals and tourists alike.

This family-owned and operated restaurant is known for its high-quality mozzarella cheese that gives you one of the longest pulls.

Some of their best-sellers include their specialty pizzas.

These pizzas are not only going to fill your belly but also make your mouth water.

Top off your meal with a decadent dessert.

Otherwise, enjoy a nice sip of your favorite alcoholic drink from their extensive selection of wine and beer.

Enjoy a Fresh & Cold Beer at Callicoon Brewing Company

Street view of the Callicoon Brewing Company

Jaclyn Vernace /

This brewpub in the town center is a relatively new establishment compared to the other businesses on Upper Main Street.

This brewery opened in 2013.

Since then, Callicoon Brewing Company has become a famous brewery that attracts beer-lovers and cider enthusiasts.

They sell freshly-brewed beers, drafts, and other beverages that are sure to refresh you after a long day of exploring and touring this lovely town.

Upon visiting, you’ll most likely catch groups of people inside, enjoying a refreshing pint of beer together.

This brewery has become one of the favorite hangout spots in town.

Its location at the heart of Callicoon also overlooks the Delaware River, giving you splendid water views when you dine outdoors on their porch.

You even have the option to purchase sandwiches, baby back ribs, steak, and more to pair with your favorite drink.

Book a Room at Callicoon Hills

Callicoon Hills is over a century old and is found roughly 15 minutes away from the heart of the town.

This resort is the perfect place to stay during your Callicoon vacation.

Hotel amenities include a king-sized pool, outdoor activities such as hiking and fishing, a cafe, and a top-notch restaurant.

This resort also offers a comfortable and relaxing ambiance to provide a refreshing experience for those wishing to rewind and escape the busy streets.

Callicoon Hills’ picturesque decor, peaceful atmosphere, and great food and drink outlets have made this place a must-visit destination.

Book a room now!

Sip on a Glass of Your Favorite Wine at Callicoon Wine Merchant

Exterior view of the Callicoon Wine Merchant

Chris Light, CC BY-SA 4.0, via Wikimedia Commons

This artisan wine shop in downtown Callicoon sells arguably the best wine this town has to offer.

You’ll find an extensive selection of your favorite wines, ranging from dry to sweet and white to red, with differing flavors.

All their bottles of wine are organic, with some even purchased from across the globe.

You may even sample a wide variety of their wines at their tasting room before purchasing a bottle.

Grab the drink that best caters to your palate.

For non-wine drinkers, Callicoon Wine Merchant offers beers, drafts, and taps.

Feel free to gather with friends and family and enjoy your wine outdoors in their sunny garden for a refreshing experience.

Shop for Local Goods at the Callicoon Farmer’s Market

People shopping at Callicoon Farmer’s Market

Chris Light, CC BY-SA 4.0, via Wikimedia Commons

Since 2000, Callicoon Farmer’s Market has been a staple in this community.

They’re best known for selling freshly made and locally grown fruits and vegetables.

However, you can find a wide variety of other items at this market, too.

Several vendors put up stalls, selling a wide range of food items and other products.

Grab ready-made food, pastries and baked goods, jams, household items, personal care products, and more.

The best part about this market is that it is a “producer-only market.”

Each vendor sells personally-made items and goods, which continues to make their local economy thrive.

This farmers’ market will complete your weekend.

There’s so much to see and buy at Callicoon Farmer’s Market, so stop by for some grocery shopping.

Shop for Vintage Items at Litt Home & Book

Litt Home & Book is a small shop found on Lower Main Street.

Known for selling vintage and pre-loved items, you can purchase various goods here.

Stroll through the aisles and skim the shelves to see all the unique items they have in store for you.

Whether you’re looking for house decor, a souvenir, or even a gift for loved ones, Litt Home & Book might have what you want.

They also sell a limited selection of books from varying genres for an affordable price.

Stop by Litt Home & Book and see what vintage item you can bring home.

Try Honey-Infused Alcoholic Beverages at Catskill Provisions Distillery

Exterior view of the Catskill Provisions Distillery

Jaclyn Vernace /

Honey and alcohol don’t go together often, but Catskill Provisions Distillery finds a way to make it work.

This distillery offers unique blends and flavors with honey-infused alcoholic beverages that hit just the right spot.

Using 100% wildflower honey, this artisan shop sells a comprehensive list of liquors.

Interior view of the Catskill Provisions Distillery

Jaclyn Vernace /

Buy honey whiskey, maple bourbon, pollinator gin, vodka, and so much more.

Though these flavors seem bold and complex, you get the chance to taste each one in their tasting room.

Grab a bottle or two of these elegant and flavorful honey-infused alcoholic drinks at Catskill Provisions Distillery.

Join the Callicoon Country Fair

Callicoon is known for hosting various events throughout the year.

One of its most sought-after events is the Callicoon County Fair.

Attracting both locals and visitors, this fair features food, music, and lots of fun and excitement.

They’ll entertain you the entire day as you meet new people.

Check out the various vendors selling different types of goods and products, or explore the historic streets of Callicoon.

This event is kid-friendly, so feel free to bring the whole family.

You can also catch other annual events, including their Art Walk, Tractor Parade, Tree Lighting, and more.

These events only get better and better each year, so stop by on your trip.

Explore the Delaware River with Lander’s River Trips

Callicoon’s location next to the Delaware River allows for many enjoyable water activities.

Lander’s River Trips will help you enjoy each of them.

Since 1955, this company has provided adventure and excitement while letting guests admire the beauty of this river.

You can go rafting, canoeing, and kayaking, or try something new like tubing.

They also allow guests to spend the night and camp on their camping grounds for a great day outdoors.

Your trip to Callicoon wouldn’t be complete without getting out on the open waters of the Delaware River.

Try Local Ciders at Seminary Hill Orchard & Cidery

Honoring cider-making traditions in Catskills, Seminary Hill Orchard & Cidery crafts some of the best ciders in the entire town.

Likewise, they only use locally sourced ingredients.

This establishment ensures high-quality ciders made just for you.

They use homegrown apples and pears harvested from their proudly local and sustainable orchard and cidery.

You can sip each freshly made cider at their tasting room and see how each drink bursts with flavor.

Watch how their ciders are made during the facility tour and see the complete production process.

Their 12-acre facility is also a sight to behold, with over 1,500 trees of 60 different varieties.

Eat Authentic Vietnamese Food at Bà & Me

Are you craving authentic Vietnamese food?

Check out Bà & Me!

Vietnamese immigrants founded the Vietnamese restaurant on Upper Main Street.

The founders wanted to bring their cuisine to the historic town of Callicoon.

Since 2012, they have served healthy and delicious food to the community with Vietnamese flavors you can’t get enough of!

You can enjoy your favorite Vietnamese dishes at this restaurant, such as banh mi, dumplings, and rice bowls.

Bà & Me has also garnered nationwide attention, appearing in upscale magazines such as The New York Times!

Achieve All-Around Wellness at River Family Wellness

After a tiring day of exploring Callicoon’s top-rated attractions, you deserve to unwind and relax.

River Family Wellness has your back.

This healing center specializes in a wide range of physical and emotional treatments.

Among these include acupuncture, massage, and even Reiki healing.

Feel good inside and out with the center’s skincare and wax sessions.

Become one with your body and regain its balance with a private yoga treatment.

And there are more treatments especially catered to your overall wellness.

River Family Wellness is on Gregory Street.

Host an Event at The Barn on Hubbard

Do you have an event coming up while you’re on your Callicoon trip?

Celebrate it at The Barn on Hubbard!

This spectacular wedding and event venue features a 19th-century dairy barn that has been around since the mid-1800s.

It sits on 18 acres of breathtaking farm property.

Its hidden alcove set within wide expanses of European gardens and pathways lit with lanterns set the scene for your romantic events.

There are also three outdoor patios, an array of vintage props ready to decorate your rustic celebration, and an annex space for cocktail sessions.

Wow your guests with the historic barn’s old-time classic appeal and large group accommodations.

The Barn on Hubbard, as the name suggests, is right along Hubbard Road.

See Vintage Tractors During the Annual Callicoon Tractor Parade

If you have an affinity for vintage vehicles, then you might not want to miss the Callicoon Tractor Parade.

This annual event is a celebration of agricultural history and raises funds for the Delaware Youth Center at the same time.

Its history started with the initiative of Kathy Langley.

She pitched the idea of a tractor show to the Callicoon Business Association in the hopes of attracting many tourists to the hamlet.

What started as a few tractors parading down Main Street eventually transformed into a hamlet-wide event that crossed many downtown roads.

Now, you can see over 300 tractors of various colors and sizes pass you by from Main and Bridge Streets.

Start your Callicoon Tractor Parade experience with a barbecue at Delaware Youth Center on Creamery Road.

View the Artisan Community at the Callicoon Art Walk

Looking for an art adventure while in Callicoon?

Make time on your schedule to attend the Callicoon Art Walk.

This annual art celebration is a fusion of art and public spaces for a deep appreciation of creative talent.

This unconventional way of presenting art makes it accessible to the general public.

Watch live performances and art displays from storefronts and the streets.

There are also dance classes, workshops, and film screenings.

And when the night comes, Callicoon transforms into an art wonderland with public art installations and workshops.

The Callicoon Art Walk takes place in the downtown area of the hamlet every October.

Listen to Live Music at Callicoon Porchfest

One of Callicoon’s anticipated festivals is the Callicoon Porchfest.

This annual festival is a free community-gathering event that takes you on a tour of the hamlet’s best shops.

Make your way across the place’s eateries, bars, and other shops.

And all the while, listen to good music at every venue and along your route.

Callicoon Porchfest is a 2-day event that’s one for the books.

Final Thoughts

Callicoon is a little town packed with so much to do and see.

Steeped in rich history, this town offers relaxation and adventure with its tourist attractions and destinations.

Enjoy community-favorite diners and eateries to historic establishments, and even water activities on the Delaware River.

You won’t run out of things to do in this town.

Whether you’re looking for a peaceful getaway or an action-packed adventure, Callicoon has it all for you.

Look no further for the ideal vacation and book a trip to the quaint and lovely town of Callicoon, New York!

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