Find Us
Pawling Chamber of Commerce
59 Charles Colman Blvd
(Not a mailing address)
845-855-0500
Hours of Operation
Monday – Friday 10 am – 4 pm
Saturday 10 am- 2 pm
Pawling Chamber of Commerce
59 Charles Colman Blvd
(Not a mailing address)
845-855-0500
Monday – Friday 10 am – 4 pm
Saturday 10 am- 2 pm
Page Contents
ToggleWhile all the restaurants in Pawling are family-friendly, there are a few that are particular favorites with the kiddos.
Even though O’Connor’s is an authentic Irish pub with a lively pub crowd, it’s also a favorite with families. The menu has lots of kid favorites like burgers and wings plus some more interesting entrees and sandwiches for the adults in the family. The service is fast and friendly, and it’s fun to eat in their courtyard when the weather is fine.
If you’re looking for a nutritious, delicious breakfast or lunch with your kids, check out this fantastic bakery. Their build-your-own breakfast sandwiches will satisfy even the pickiest eater. For lunch, they offer kid-friendly favorites like crispy chicken sandwiches and grilled cheese with homemade tomato soup. They even make their own potato chips here. And of course, kids can choose from a huge variety of scrumptious cookies and cupcakes for dessert!
If you love a country diner, especially an old school diner where all the food tastes like Grandma made it, take the family to this local favorite. Open for breakfast and lunch, their huge menu includes comfort food favorites like french toast, pancakes, burgers, fried chicken, and meatloaf with mashed potatoes.
Let’s face it, you can’t go wrong with pizza for a kid-friendly lunch or dinner. If you visit Village Pizza, ask about their “Dessert Pizza”–it’s a masterpiece of Italian desserts on a pizza! Their soups and salads are also terrific for parents who are looking for a non-pizza lunch option.
This isn’t just a toy store, it’s a “destination” toy store that carries new toys and specializes in an amazing collection of vintage toys. Featured on the series “A Toy Store Near You,” a visit to this local store is a bonding experience for the whole family, as the adults experience intense nostalgia seeing favorite childhood toys that they’d forgotten even existed. So many opportunities to give our kids a valuable cultural education while they pick out a new toy or two for themselves!
This gift shop carries lovely gifts for folks of all ages, and has a delightful selection of gifts and toys for infants and young children. (This is also a great place to find Pawling “swag” like caps and hoodies, as well as local maple syrup and other specialty food items.)
This gem of a bookstore has a great kids’ section that includes a carefully curated selection of books and educational toys for kids of all ages. They also have a great young adult selection for the teens in the family.
If you run out of diapers, snacks, ibuprofen, crayons, coloring books, etc., the Pawling CVS is conveniently located in the village within walking distance of the train station and the Station Inn.
Lakeside Park has two playgrounds for the little ones, one of them is situated near the beach and overlooks the lake. Lakeside also has soccer fields, a gaga pit, a basketball court, a fitness trail, hiking trails, a dog park and a frisbee golf course.
Murrow Park has one playground with swings and play structures for both older and younger children. Murrow Park also has a basketball court and hiking trails.
Pawling Elementary School has two large playgrounds. They are only open to the public when school is not in session. The playground to the left of the school is for younger children. The playground near the parking lot is for older kids. There are also baseball fields and a basketball court here.
Lakeside Park Waterfront (2 Lakeside Drive)
During the summer (between Memorial Day and Labor Day) the waterfront is open on weekends and during the week when school is not in session. The waterfront includes a sandy beach and well-maintained swimming area surrounded by floating docks and fully staffed with lifeguards during open hours. The swimming area also includes bathrooms, picnic tables, outdoor grills for cooking, and a variety of kayaks, row boats and standing paddle boards that are included at no extra charge with your day pass to the waterfront. Both residents and non-residents can purchase day passes to the waterfront at Lakeside Park.
At Lakeside Park, there’s also an easy trail around the lake that is perfect for kids, which includes an outdoor chapel, interesting rock formations and views of different sections of the lake.
Managed by the Nature Conservancy, this preserve includes several hiking trails, including part of the Appalachian Trail. Educational markers along the trail provide information about native plants, animals and Native Americans along the way. Sights include swamps, streams, small waterfalls and ancient rock formations. A trail map can be found here: https://www.dutchessny.gov/Departments/Parks/docs/tmspawlingnaturereserve.pdf
This is an easy hike for kids from the parking lot to the lake. In spite of its name and related history as the site of a former nuclear research facility, Nuclear Lake is a pristine and lovely place to visit. The Appalachian Trail connects to the trail beyond the lake, if you’re looking for a longer, more challenging hike.
This hike might not be suitable for the youngest hikers, because it is quite a steady climb, but it is well worth the incredible view from Cat Rocks at the top. It begins at the Dover Oak, where there is a little parking area. The Dover Oak is the largest white oak tree on the entire Appalachian Trail and has a massive trunk. Because this hike is a section of the Appalachian Trail, you might even meet some thru-hikers on your way. If the kiddos need a break, stop by the Telephone Shelter and Little Free Library, which are about ⅔ of the way to Cat Rocks.
The Maybrook Trailway is a flat paved trail, excellent for walking and biking. If you follow the trail North from this parking area, you will see sections of beautiful Whaley Lake. For those who are more adventurous and physically fit, you can bike to interesting attractions in other towns, including the Walkway Over the Hudson in Poughkeepsie. (Because this is part of the Empire State Rail Trail, you could actually bike or walk from Manhattan to Pawling and points north on this trail.)
During the winter months, Lakeside Park has a temporary ice skating rink set up under the pavilion near the Teen Center. The rink is open during the park’s open hours and admission is free. Children must be supervised and all skaters must wear a helmet. Visitors to the park can also enjoy sledding and cross country skiing: please call the Town of Pawling Recreation Department for more information.
It’s always snowy on the mountain at Thunder Ridge–at least it is after the first big freeze in winter every year. Located at 137 Birch Hill Road, just 10 minutes away in Patterson, Thunder Ridge has 22 trails, 3 chair lifts, 4 magic carpets, and has slopes suitable for all ages and abilities. Onsite dining is available at the Slope Side Cafe. They offer a variety of classes and events throughout the season, and there’s even a free shuttle between the slopes and the Patterson Metro-North Station for folks who want to visit via train. To learn more, visit https://thunderridgeski.com/
If you’re new to skating or don’t own your own skates, the Brewster Ice Arena offers skate rentals as well as instruction for skaters of all ages and levels of expertise. Located at 63 Fields Lane in Brewster, it’s a twenty-minute drive south from Pawling.Their facility has 3 indoor rinks, skate rental, a pro shop, a snack bar, and a restaurant that are open year-round. In the winter, they also have an additional outdoor rink. To learn more and to view the open skating schedule, go to https://brewstericearena.com/seasonal-schedule.
The Gunnison Natural History Museum, located in the basement of the Akin Free Library on Quaker Hill, is a fascinating place to visit for both adults and children. Donated to the Akin Free Library in 1960 by private collector Olive Gunnison, the collection is both educational and entertaining. The extensive collection is divided into two sections, a natural history collection and a “cabinet of curiosities.”
Collection highlights include a 10-lb. piece of optical quality quartz from Brazil, a collection of over 175 different birds’ eggs and about 50 nests, and several specimens of now-extinct animals: the passenger pigeon and the heath hen, and the ivory-billed woodpecker. Young visitors can enjoy a few interactive exhibits as well–a light switch allows you to see a snake, and then the skeleton of the snake. Another display shows which mushrooms are poisonous. Yet another display allows visitors to explore fluorescence with a black light.
The Pawling LIbrary has an excellent children’s and young adult book collection and many great programs for young folks. Not only are there lots of great books to keep young visitors entertained, they also have a large collection of puzzles and board games, as well as computers with age-appropriate games in the children’s section and the teen room.
Yes, George Washington did indeed sleep here, while his Army was headquartered in Pawling during the Revolutionary War.. Even if your children are not very interested in history, it’s worth a visit to check out the model train display of Pawling Village in 1948. For more information about this and other local historic sites: pawlinghistory.org
Does your family enjoy mini golf? There are two places near Pawling to go, and each of them is attached to a great ice cream and casual food restaurant.
In Dover Plains, about a 10 minute drive north of Pawling, check out Kelly’s Creamery and Kelly’s Husband’s Food Truck (3202 NY-22, Dover Plains). The food and ice cream are superb, there’s a fire pit and corn hole in the outdoor dining area, and the golf course is fairly new and fun to play.
In Brewster, about a 20 minute drive south of Pawling, check out the Red Rooster Drive-In (1566 NY-22, Brewster). The vibe of this place is retro 1950’s fast food and ice cream, with both indoor and outdoor dining options. Amenities include a few small coin operated rides and a classic mini golf course, complete with rooster statue.
There aren’t a lot of drive-in movie places left in the United States, but luckily we still have a few of them here in the Hudson Valley. If you have fond memories of going to the drive-in and would like to share them with your children, check out the Four Brothers Drive-In (4957 NY-22, Armenia), about a 30 minute drive north in Amenia. More than just a drive-in theater, this is a total retro experience. Visitors can enjoy a full meal on the patio of the Four Brothers Restaurant or enjoy fun variations of classic snacks and creative cocktails from the Grand Shack. Coin-operated rides and other activities will keep the kiddos entertained until the movie starts, and you can even reserve an Airstream trailer and spend the night!
This isn’t actually a church, but a small town nature preserve in Dover Plains, 20 minutes north of Pawling. There are a few excellent hiking trails here, but the main attraction is the “stone church”, a cave-like rock formation with a 30-ft waterfall inside that flows through the “cave” and out into a stream. First mentioned in print in the 1600’s, the cave has a fascinating history and was important to local Native Americans. There is no parking area adjacent to the preserve, but there are a few places where visitors are encouraged to park, including the Dover Elementary School parking lot across the street. For more info: https://www.nynjtc.org/park/dover-stone-church-preserve?fbclid=IwAR2_217HjAFfiKReIIQH0eIfuxoTcJNgf1m5y5yOiyGYMqnJfm4KK42l264
About a forty minute drive from Pawling, the Walkway Over the Hudson is the world’s longest elevated pedestrian bridge, spanning the Hudson River between Poughkeepsie and Highland, NY. The bridge is open from dawn to dusk year round, but the busy season is during the warm months, when the elevator is open and they host special events. The views of the river and surrounding towns are spectacular, and the bridge is wide enough to accommodate pedestrians, strollers, bikes, scooters and dog walkers. The walkway is 1.28 miles long from gate to gate and stands 212 feet above the river. Bathrooms, information kiosks and food vendors are located on both sides of the bridge. The walkway also hosts special nighttime events, with movie nights in the park under the bridge on the Poughkeepsie side, and Walkway at Night, where visitors can walk the bridge from sunset into the evening for a small donation fee. For more info, visit https://walkway.org/
Located near the Walkway Over the Hudson and two riverfront parks, this museum for young children has many fun early literacy and early STEM exhibits that encourage little ones to learn through play. This place is perfect for little kids who are getting bored and antsy stuck inside on a rainy day. For more info, visit https://mhdm.org/
Just a 40-minute drive from Pawling, DIA Beacon is a modern art museum located in the town of Beacon, NY, which also has many fabulous restaurants, shops and hotels. While this isn’t a children’s museum, many of the exhibits feature the kind of art that can be particularly fun for children to experience, like their giant Richard Serra sculptures that people can walk inside. For more info, visit https://www.diaart.org/visit/visit-our-locations-sites/dia-beacon-beacon-united-states
