Upstate New York is a fantastic choice for a two-day getaway, especially in early fall when the foliage is just starting to turn. You’ll be treated to stunning views, and there are plenty of toddler-friendly hikes and beautiful waterfalls to explore. Let’s dive into your ideal itinerary!

Day 1: Exploring the Beauty of the Hudson Valley

Morning:

• Breakfast in Beacon: Start your day with a cozy breakfast at a local café like The Beacon Bread Company. They have delicious pastries and coffee to fuel your adventure.

• Visit the Dia:Beacon: After breakfast, take a quick stroll to the Dia:Beacon, a contemporary art museum housed in a former Nabisco box factory. While the art might be more for the adults, the spacious grounds are perfect for your toddler to roam around.

Mid-Morning:

• Hike at Mount Beacon: Just a short drive away, Mount Beacon offers a toddler-friendly hike. The trail is about 1.5 miles round trip and has some gentle inclines. The views from the top are absolutely breathtaking, especially with the fall colors starting to pop!

Lunch:

• Picnic at Long Dock Park: Pack a picnic or grab some sandwiches from a local deli and head to Long Dock Park. It’s a lovely spot by the river with plenty of space for your little one to play and enjoy the scenery.

Afternoon:

• Visit Kaaterskill Falls: After lunch, drive to Kaaterskill Falls, one of the most iconic waterfalls in the Catskills. The hike to the viewing platform is short and easy, making it perfect for toddlers. The sight of the cascading water surrounded by vibrant fall foliage is simply magical!

Evening:

• Dinner in Tannersville: Head to Tannersville for dinner. The Last Chance Antiques & Cheese Café is a charming spot with a cozy atmosphere and a menu that caters to all tastes.

• Stay Overnight: Consider staying at a family-friendly inn or a cozy cabin in the area. The Catskill Mountain Lodge is a great option with beautiful views and easy access to nature.

Day 2: Waterfalls and Scenic Drives

Morning:

• Breakfast at the Lodge: Enjoy a hearty breakfast at your lodge or a nearby café to start your day right.

Mid-Morning:

• Visit the Olana State Historic Site: After breakfast, take a short drive to Olana, the home of artist Frederic Edwin Church. The grounds are stroller-friendly, and the views of the Hudson River Valley are stunning, especially in the fall.

Lunch:

• Lunch in Hudson: Head to the charming town of Hudson for lunch. The Crimson Sparrow offers a lovely menu, or you can grab something quick at a local café.

Afternoon:

• Hike at Bash Bish Falls: After lunch, make your way to Bash Bish Falls State Park. The hike to the falls is about a mile and is relatively easy, making it perfect for families. The falls themselves are gorgeous, and there’s plenty of space for your toddler to explore safely.

Late Afternoon:

• Scenic Drive through the Berkshires: After visiting the falls, take a scenic drive through the Berkshires. The winding roads and colorful foliage will be a treat for the eyes. You might even spot some charming little towns along the way!

Evening:

• Dinner in Great Barrington: Wrap up your trip with dinner in Great Barrington. The Prairie Whale is a great spot for farm-to-table dining, and they have a relaxed atmosphere that’s perfect for families.

• Head Home: After dinner, it’s time to head back home, filled with beautiful memories and stunning photos of your fall adventure in upstate New York!

I hope this itinerary gives you a wonderful mix of nature, art, and delicious food, all while being toddler-friendly! Enjoy your trip! 🍂🌊🏞️