9 Road Trips to Explore With Your Family Near Westchester

Road Trips Near Westchester

Road Trips to Explore With Your Family Near Westchester

While you may love traveling with your kids, taking planes or going far away is sometimes not practical or affordable. One way to enjoy nearby areas is to take family road trips! We love road trips spring break or the summer. During this time, load up the car and plan a fun week or weekend away. Not only can you avoid lengthy trips but you’ll have your own car for exploring and discovering. Read on to check out some nearby destinations and road trips to enjoy with your kids.

Psst..looking for more travel ideas? Check out Rethinking the Family Vacation: Intentional Travel (a new kind of trip)

Lake Placid, NY

A little over four hours away from Westchester, a trip to Lake Placid offers the perfect meld activities and nature. Enjoy stunning views of Lake Champlain and history as the location of the 1932 and 1980 Olympics.

The area is in famous for its many nearby hikes. This includes adventures to waterfalls, such as the towering Roaring Brook Falls (Roaring Brook Falls Trail, Keene Valley, NY 12943); Cascade Falls (NY-73 Scenic, Keene, NY 12942 ); Wilmington Flume (5348 NY-86 Scenic, Wilmington, NY 12997); and the 8.5 mile Rainbow Fall Loop.

For those traveling in the winter, enjoy access to its many ski areas. Check out the iconic Whiteface Mountain, the fifth-highest mountain in New York State or the Jackrabbit Ski Trail Access (Lake Placid, NY 12946)

For activities, take the kids to Lake Placid Olympic Museum to learn more about the history of the games (2634 Main St, Lake Placid, NY 12946); Mt Van Hoevenberg for some indoor climbing (31 VanHoevenberg Way, Lake Placid, NY); and swimming at Mirror Lake Beach (Parkside Drive, Lake Placid, NY). Be sure to add a a visit to The Wild Center in Tupper Lake for a day of discovery and a visit to the gorgeous John Brown Farm State Historic Site.

For a very different family adventure, try a Lake Placid Toboggan Chute (Mirror Lake, Lake Placid, NY). Families will also love its sweet and quaint town. Spend a day strolling along Main Street and hopping into all of the shops. Some favorites include Emma’s Lake Placid Creamery (2507 Main St, Lake Placid, NY 12946) and The Coffee Bar (2527 Main St, Lake Placid, NY 12946). Plus, shops with Adirondack-inspired items from Pure Placid or the Adirondack Trading Company.

Hudson, NY

This town is around one hour and 30 minutes away from Westchester. Here, you will discover incredible dining options, shopping, waterside activities, art museums, access to nature, and more. Check out Basilica Hudson for an arts and cultural event (110 South Front Street, Hudson, NY 12534); a visit to the FASNY Museum of Firefighting to view a cool collection of American firefighting artifacts, along with 90 vintage and rare fire engines (117 Harry Howard Avenue, Hudson, NY 12534); visit Hudson Hall, New York state’s oldest surviving theater (327 Warren Street, Hudson, NY 12534); or explore the 250-acre landscape of the historic Olana State Historic Site (5720 New York 9G, Hudson, NY 12534).

For hiking and outdoor adventures, explore the 750-mile Empire State Trailhead, Promenade Hill Park (2 Warren St, Hudson, NY 12534), or the Greenport Conservation Area (319 Joslen Blvd, Hudson, NY 12534), to name a few options.

You can also enjoy a trip on the Hudson Ferry Co by taking a trip to Athens. Enjoy waterside activities and rent a paddleboard from Hudson Paddles (Henry Hudson Riverfront Park, 108 Water Street, Hudson, NY). Checking out restaurants is a must in Hudson. For sweets try Culture Cream (318 Warren St, Hudson, NY) and 225 Scoops (223 1/2 Warren Street, Hudson, NY 12534). For pizza, check out Baba Louie’s Sourdough Pizza (517 Warren Street, Hudson, NY 12534) and the Hudson Sandwich Shop for quick bites (430 Prison Alley, Hudson, NY 12534), as well as the Hudson Brewing Company to see Hudson’s first brewery since prohibition.

Cold Spring, NY

This quaint town is only 45 minutes to an hour away from Westchester. Stroll along Main Street as you walk into its many charming shops. Some favorites include Cold Spring Antiques Center (77 Main Street Cold Spring NY 10516), Hudson Rogue (255 Main Street, Nelsonville NY, 10516), and Antipodean Books, Maps, & Prints (29 Garrison Landing, Cold Spring, NY), to name a few options. Bring home some sweet treats from the Cold Spring Candy Co. and Fudge Factory (11 Main Street, Cold Spring, NY 10516) , a vintage-style candy store.

Check out Hudson River Expeditions (14 Market St., Cold Spring, NY 10516) to rent a kayak, canoe, or paddleboard. For hiking, check out gorgeous views of the Hudson River at Little Stony Point (3007 Bear Mountain-Beacon Hwy, Cold Spring, NY 10516) or Hudson Highlands State Park (3260 NY-9D, Cold Spring, NY 10516). For some playground fun, check out Cold Spring Tiny Tots Park (4 High St, Cold Spring, NY 10516). Find a sand pit, tons of  mini bikes, swings, slides, and more.

For arts and culture in the summer, see an outdoor performance at the Hudson Valley Shakespeare Festival (2015 US-9, Garrison, NY 10524) or the Philipstown Depot Theatre (10 Garrisons Landing, Garrison, NY 10524).

Stamford, CT

At only 30 minutes from Westchester, families can enjoy a regular adventures in Stamford. Check out the Stamford Nature Preserve (39 Scofieldtown Rd, Stamford, CT 06903) and enjoy access to 80 acres of nature trails. Kids will also love a visit to Heckscher Farm to view farm animals and explore the Overbrook Nature Center, Trails and Nature’s Playground. Here, you can also explore the historic Bendel Mansion, special art exhibits, and nearby trails. The Barlett Arboretum and Gardens (151 Brookdale Rd, Stamford, CT 06903) is also a fun place to walk and enjoy its 13 gardens, arts and crafts, and special events.

For live theater and kids’ shows, check out The Palace Stamford (61 Atlantic Street, Stamford, CT 06901) with upcoming productions of Bluey Live and Sesame Street Live. For hiking, enjoy the gentle path at the Mianus River Preserve (Merriebrook Ln, Stamford, CT 06902), the Helen Altschul Preserve, and the Newman Mills Park (310 Riverbank Rd, Stamford, CT 06903).

Lancaster, PA

For a longer road trip (around three and a half hours from Westchester), take a trip to Lancaster. Here, you and your kids can learn more about Amish living. Additionally, enjoy the areas many beautiful farms and contemporary activities. For outdoor adventures, enjoy access to Susquehanna Heritage (1706 Long Level Rd, Wrightsville, PA 17368) with beautiful views along the Susquehanna River and hiking along the Columbia Crossings River Trails Center(41 Walnut St, Columbia, PA 17512).

Additionally, find over eight county parks. This includes Chickies Rock County Park (880 Chickies Hill Rd, Columbia, PA 17512), Overlook Park, and Long’s Park, to name a few options. For farming adventures, visit Cherry Crest Adventure Farm (150 Cherry Hill Rd, Ronks, PA 17572). Kids will love spending a day at the farm to see and pet farm animals. Plus, participate in an interactive maze, enjoy 2.5 miles of paths, a paintball range, and much more. Finally, throughout the year they offer several festivals. This includes the baby animal festival, the cider donut festival, and the sweet corn festival.

Additionally, enjoy a visit to the Eastland Alpacas and its 30-acre farm (2089 Risser Mill Road, Mount Joy, PA 17552), the Indian Echo Cavern to discover natural unground beauty, and the Amish Farm House (2395 Covered Bridge Drive, Lancaster, PA 17602) to learn all about Amish living.

Philadelphia, PA

While trips to nearby NYC are exciting, try visiting another local city with a trip to Philly. A trip to Philadelphia is a fun way to learn more American history that’s only two hours from Westchester. Plus, enjoy museums, art, food, walking tours, and much more.

For history and museums, visit the Liberty Bell (526 Market St, Philadelphia, PA 19106), the Benjamin Franklin Museum (Franklin Court. Entrance to the courtyard is from Market or Chestnut Street, between 3rd and 4th Streets), The President’s House: Freedom and Slavery in the Making of a New Nation, and The African American Museum (701 Arch St, Philadelphia, PA 19106), to name a few options.

There is also plenty to do in Philly with the kids. Enjoy visits to the interactive Please Touch Museum (4231 Avenue of the Republic, Philadelphia, PA 19131). The Franklin Institute is a lot of fun with its ode science and technology (222 N 20th St, Philadelphia, PA 19103), the Philadelphia Zoo (3400 W Girard Ave, Philadelphia, PA 19104). Enjoy Franklin Square and its seven acres of nature and carousel rides. Plus, a day at the nearby Adventure Aquarium (1 Riverside Dr, Camden, NJ 08103). Add nearby The Bucks County Children’s Museum (500 Union Square Dr, New Hope, PA 18938) and Longwood Gardens (1001 Longwood Rd, Kennett Square, PA 19348) to your list. For endless fun for younger kids, visit Sesame Place (100 Sesame Rd, Langhorne, PA 19047).

Philly Food

Food and drink options are endless in Philly, including classics and award-winning restaurants. For classic cheesesteaks, visit Geno’s Steaks (1219 S 9th St, Philadelphia, PA 19147) and Pat’s King of Steaks (1237 E Passyunk Ave, Philadelphia, PA 19147). If you’re looking for a hoagie, check out Cosmi’s Deli (1501 S 8th St, Philadelphia, PA 19147) and Angelo’s Pizzeria South Philly (736 S 9th St, Philadelphia, PA 19147). Gravy pasta dinner is another Philly classic to try at Villa di Roma (936 S 9th St, Philadelphia, PA 19147) or Ralph’s Italian Restaurant (760 S 9th St, Philadelphia, PA 19147)

Boston, MA

Another fun nearby city to visit is Boston! At around three hours away from Westchester, Boston offers another great opportunity to learn more about the history. Kick-off your travel experience with a visit to the Boston Museum of Science ( Museum Of Science Driveway, Boston, MA 02114) and the New England Aquarium. Younger kids will love the interactive Boston Children’s Museum (308 Congress St, Boston, MA 02210) and Martin’s Park & Playground for some outdoor play.

Another fun way to experience the city is stroll around the stunning Boston Public Garden, or take a fun ride on a swan boat .

For history, enjoy a visit to the Boston Tea Party Ship & Museum, a tour of the 200-year-old Old Ironsides, and the Bunker Hill Monument. Additionally, check out the Black Heritage Trail, the historic Faneuil Hall Marketplace (4 South Market Street, 5th Floor, Boston, MA 02109), and the path of presidents with visits to Longfellow House. This includes Washington’s Headquarters, Harvard University, Widener Library, and the birthplace of JFK.

Mystic, CT

This quaint seaside town is around two hours away from Westchester. You and our kids can enjoy tons of attractions, restaurants, and cute shops. Start the Mystic Aquarium (55 Coogan Blvd, Mystic, CT 06355) to learn more about and see a collection of sea lions, beluga whales, penguins, fur seals, and much more. Enjoy a visit to the Mystic Seaport Museum (75 Greenmanville Ave., Mystic, CT) to learn more about marine life. Rent a paddle board, bike, or snowboard from Adventure Mystic (15 Holmes Street, Mystic, CT).

Nature lovers will enjoy Williams Beach Park. Additionally, there’s the Avalonia Land Conservancy with a hide and seek scavenger hunt, as well as Haley Farm State Park, one of Connecticut’s Colonial-era farms.

Additionally, Mystic is home to a charming downtown area. Take a stroll and enjoy access to over 80 independent shops. Grab a sweet treat at Mystic Drawbridge Ice Cream or Kenzie’s Fudge and Chocolate Shop. Kids will love the fun and cozy Mystic Diner. Seafood fans will love Abbott’s Outpost, Oyster Club, and Ford’s Lobster.

Woodstock, NY

This idyllic upstate town is home to a combination of small shops, restaurants, and nature. Families can enjoy nearby hikes such as Shawangunk Mountains, Overlook Mountain Trailhead (353 Meads Mountain Rd, Woodstock, NY), Sloane Gorge Preserve (487 Stoll Road, Woodstock, NY 12498), the Thorn Preserve – Catskill Center (55 John Joy Road, Woodstock, NY 12498), Kaaterskill Wild Forest (70 Catskill View Circle, Saugerties, NY 12477) to see waterfalls, or the flat Comeau Property Trail (95 Comeau Drive, Woodstock, NY 12498), to name a few.

The spring and summer is a great time to visit to enjoy the areas many lakes and reserves. This includes Big and Little Deep, Cooper Lake, or the Millstream Swimming Hole. The downtown area is bustling with small shops to explore. This includes the sweet kids’ toy store, Tinker Toys (5 Mill Hill Rd, Woodstock, NY 12498) and The Golden Notebook (29 Tinker St, Woodstock, NY 12498).

Additionally, other check out the World’s Largest Kaleidoscope at Emerson Resort, Bethel Woods Center for the Arts (200 Hurd Rd, Bethel, NY 12720), and the Catskill Animal Sanctuary.