10 Easy Out-of-County Road Trips from Poughkeepsie, NY
Planning a day trip from Poughkeepsie and want to get out of Dutchess County for a bit? You’re in luck. Within about an hour or so, you can find mountain views, farm stands, lakes, historic towns, and some seriously good food.
All of these road trips start from Poughkeepsie and head into nearby counties like Ulster, Orange, Columbia, Putnam, plus Western Connecticut and the Berkshires in Massachusetts. No need for a full vacation—just hop in the car, grab a coffee, and go.
1. New Paltz & Mohonk Region (Ulster County, NY)
If you only have time for one road trip from Poughkeepsie, this is the classic.
Cross the Mid-Hudson Bridge and in about 25–35 minutes you’ll be in
New Paltz, a laid-back college town with big mountain vibes.
Things to do:
- Walk the historic Huguenot Street district – One of the oldest streets in the country, lined with stone houses and big shade trees.
- Hike or walk in the Shawangunks (“The Gunks”) – Even if you’re not a hardcore hiker, there are easy trails with sweeping valley views.
- Visit Mohonk Preserve – Day passes give you access to miles of trails, cliffs, and carriage roads.
- Stroll Main Street – Cafés, ice cream, used bookstores, and outdoor gear shops.
On clear days you can see forever from some of the overlooks. It feels like you’ve driven to another state, but you’re still under an hour from home.
2. Woodstock & the Catskills Gateway (Ulster County, NY)
About 45–60 minutes from Poughkeepsie,
Woodstock is the perfect mix of artsy, cozy, and outdoorsy.
Why go: If you’re in the mood for galleries, music, and a little mountain air, this is your spot.
Things to do:
- Explore Tinker Street – Shops, art galleries, and cafés where you’ll want to linger.
- Check out live music – Many small venues and bars have live shows, especially on weekends.
- Head out for a short Catskills hike – Look for well-known easy hikes or scenic trailheads just outside town.
- Grab a bite – Farm-to-table spots, pizza, and bakeries are easy to find.
Woodstock makes a great day trip from Poughkeepsie if you like a small-town vibe with a creative twist.
3. Kingston’s Historic Waterfront (Ulster County, NY)
Just north of the bridge from Poughkeepsie, about 35–45 minutes away, you’ll find
Kingston, one of the Hudson Valley’s most interesting small cities.
Highlights:
- Wander the Rondout waterfront – Old brick warehouses, river views, and boats along the dock.
- Visit the Hudson River Maritime Museum – Learn about river history and boat life in a compact, easy-to-enjoy space.
- Explore Uptown Kingston – Cobblestone streets, boutiques, and historic buildings.
- Grab a riverfront meal – Several restaurants offer outdoor seating when the weather’s nice.
Kingston is an easy, low-stress road trip from Poughkeepsie: park once, walk a lot, eat well, and enjoy the river.
4. Cold Spring on the Hudson (Putnam County, NY)
Looking for a classic small Hudson River town? About 35–45 minutes south of Poughkeepsie,
Cold Spring gives you that postcard-perfect main street plus mountain views across the water.
Things to do in Cold Spring:
- Walk Main Street – Antique shops, home décor, ice cream, and coffee spots line the street down to the river.
- Relax at the riverfront park – Sit on a bench, watch the trains and boats, and soak in the scenery.
- Try a short hike nearby – The area is known for more challenging hikes, but you can find easier trails and viewpoints if you prefer.
- Pick a cozy café or pub – Ideal for a late lunch or early dinner before heading back.
Cold Spring makes an excellent half-day trip from Poughkeepsie when you want a relaxed, walkable place with great Hudson River views.
5. Beacon’s Art & Food Scene (Dutchess Border / Use as a Stopover)
While Beacon itself is in Dutchess County (so we’re not counting it as a main destination), it’s a useful
stopover city on your way to
Putnam or
Orange County trips. Many people pair Beacon with a visit to Cold Spring or the Newburgh waterfront across the river.
If you’re planning a loop, think about:
- Starting in Poughkeepsie
- Grabbing coffee or brunch in Beacon
- Continuing on to Cold Spring or over the Newburgh–Beacon Bridge into Orange County
Using Beacon as a quick stop is a smart way to break up the drive and add more variety to your road trip from Poughkeepsie.
6. Newburgh Waterfront & Orange County Views (Orange County, NY)
Cross the river into
Newburgh, about 35–45 minutes from Poughkeepsie, and you’ll find a long stretch of Hudson Riverfront packed with restaurants and big views of the mountains and bridges.
What to do:
- Walk the waterfront walkway – Wide, flat, and perfect for a slow stroll.
- Pick a restaurant with outdoor seating – Ideal for date nights or a relaxed lunch with friends.
- Take in the views of Beacon and Mount Beacon – The scenery is stunning, especially near sunset.
From Newburgh, you can also drive a bit farther into Orange County to explore local farms, wineries, or small towns if you want to stretch your day.
7. The Berkshires: Great Barrington Getaway (Berkshire County, MA)
Ready for a slightly longer adventure? In about 1.5 hours, you can go from Poughkeepsie to
Great Barrington in the Berkshires of western Massachusetts.
This trip feels more like a mini-vacation even if you’re just gone for the day.
Why it’s worth the drive:
- Charming downtown – Local shops, bakeries, and small-town New England architecture.
- Outdoor activities – Lakes, gentle hikes, and scenic overlooks nearby.
- Seasonal fun – Leaf-peeping in fall, cozy cafés and small ski areas in winter.
If you like the idea of leaving New York for the day without flying anywhere, Great Barrington is a fantastic road trip from Poughkeepsie.
8. Hudson: Artsy, Historic & Walkable (Columbia County, NY)
About an hour north of Poughkeepsie,
Hudson has become a major Hudson Valley destination, especially for design lovers, foodies, and anyone who likes a good stroll.
Things to do in Hudson:
- Warren Street – The main drag is lined with vintage shops, home décor stores, art galleries, and cafés.
- Riverfront Park – Walk down toward the Hudson River for open views and fresh air.
- Dining – From upscale restaurants to casual bakeries, there’s plenty of choice.
Hudson pairs nicely with nearby scenic backroads in Columbia County if you want to add a short country drive after lunch.
9. Litchfield Hills & Northwest Corner Towns (Northwest Hills Region, CT)
Head east from Poughkeepsie and cross into Connecticut’s
Northwest Hills. In about 1–1.5 hours, you’ll reach a world of rolling hills, historic villages, and old stone walls along the roads.
Some towns to plug into your GPS:
- Litchfield
- Kent
- New Preston
Ideas for your day:
- Wander small-town main streets – Think white church steeples, country stores, and classic New England style.
- Visit a lake or state park – Many spots offer easy walking paths and picnic areas.
- Stop at a farm market or bakery – Perfect for grabbing local jams, pies, or snacks.
This is a peaceful road trip from Poughkeepsie when you want quiet beauty and a slower pace.
10. Danbury & Western Connecticut Day Trip (Western Connecticut Region, CT)
For an easy interstate-style road trip, head toward
Danbury and the surrounding Western Connecticut area, roughly 1–1.25 hours from Poughkeepsie.
What you can do:
- Explore downtown Danbury – Restaurants, shops, and parks give you options for a relaxed afternoon.
- Visit nearby lakes – The region has several lakes and reservoirs with scenic overlooks and picnic spots.
- Check out local shopping – If you’re in the mood for a practical trip, you’ll find plenty of stores.
This is a good choice if you want a simple, straightforward day trip with easy highway access from the Poughkeepsie area.
Tips for Planning Your Poughkeepsie Road Trips
To make the most of these short out-of-county trips from Poughkeepsie, consider a few basics:
- Leave early – You’ll hit less traffic and have more time to explore.
- Check hours ahead of time – Small-town shops and museums sometimes close earlier than big-city places.
- Pack the basics – Water, snacks, a light jacket, and comfortable walking shoes go a long way.
- Think seasonally – Leaf season, summer lake days, and winter holiday lights all change how each place feels.
If you’re like many people in the Hudson Valley, you’ll find that these day trips start to become your go-to weekend plans. It’s amazing how different each direction from Poughkeepsie feels within just an hour or so of driving.
Share Your Favorite Day Trips from Poughkeepsie
Have you taken any of these road trips from Poughkeepsie, NY? Do you have a favorite small town, hike, or hidden gem in Ulster, Orange, Columbia, Putnam, Western Connecticut, the Northwest Hills, or the Berkshires?
I’d love to hear from you.
- Drop a comment with your favorite out-of-county day trip.
- Share this post with friends or family who live in or near Poughkeepsie and are always saying, “There’s nothing to do this weekend.”
Your tips and stories help other travelers discover new places, so don’t be shy—share your best Poughkeepsie-area road trip ideas below!
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