Road Trip Inspiration: It’s Time to Start Planning for Fall!

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Road Trip Inspiration: It’s Time to Start Planning for Fall!

As the leaves change color, the weather gets cooler, and the pumpkin spice craze takes over, we’re all starting to feel the fall vibes. And what better way to enjoy the fall than with a family road trip? The best part about road trips is that they’re not as complicated to plan as a full vacay, and you can easily turn them into day trips if that works best for your schedule. Lucky for us NYC families, there are some road trip treasures just hours away. If you’re looking to plan a quick getaway that your whole family will love, then check out these road trip ideas for the fall!

Psst… Check out The Best Hayrides Near New York City to Visit This Fall 2021!

Annapolis & Anne Arundel County

We love the history embedded in this fun family road trip! From culturally and historically rich museums like the Banneker-Douglass Museum to yummy eats & treats like Dangerously Delicious Pies, we can’t get enough of this place. Your kids may also like the Smithsonian Environmental Research Center, where you can hop on hiking trails or launch your kayak for an outdoor adventure.

Rockland County

For families looking for adventure and gorgeous scenery, you are going to want to head to Rockland County. If you’re looking for an outdoor escape, Rockland County has beautiful fall foliage, hiking trails, apple and pumpkin picking, street fairs and more. We recommend Dr. Davies Farm or The Orchards of Concklin for a farm adventure! Get in the fall spirit with a family trip to Rockland County this season. In Rockland County’s Rivertowns, enjoy a range of activities with spectacular views of the Hudson River. Find several parks stretching north to south, where there’s plenty of public space to access the water. You can camp and fish in Haverstraw, sail or go tubing along the coast of Nyack, or canoe through the marshes off Piermont.

Hudson County

New Jersey has some gems that are not too far from the city, and one of them is Hudson County! You don’t want to miss the two big events of the fall: the 31st Annual JCAST and All About Downtown. At JCAST (Sept 30-Oct 3), the largest art tour in NJ, you can explore artists, curated tours, kid events and more. All About Downtown (Sept 18) is a street fair with local businesses, kids rides, face paint, beer gardens and live music. Hudson County has lots of events coming up in the fall, so mark your calendars now. 


Newport is the perfect place to bring your family for a quick getaway this fall. From unparalleled seafood to charming seaside resorts, beaches, shopping and kid-friendly activities, you will have plenty to do. If you’re curious about the options for kids, we recommend checking out the craft classes at Cutie Curls Boutique or the Scavenger Hunt Bingo at NBS. We’ve also got the scoop on the new Marble House Family/Kids Tour, designed for kids under age 13. A professional voice actor plays the role of Marble House, which Alva Vanderbilt regarded as her “fourth child.” The house speaks in a friendly voice, guiding young visitors to see the “little things” that tell a big story. This is the perfect activity for the whole family, because little ones and bigger kids alike can join in on the educational fun. And for the parents, we know you’ll love the Wine + Cheese sail. Great for a date night or just a fun evening with friends, it doesn’t get much better than wine and gourmet cheeses!

New Hampshire

A perfect road trip is one to a charming destination. Pack up the family or head over for some me-time at The Inn at East Hill Farm (1-800-242-6495 ). This is a working farm located in the southwestern corner of New Hampshire; this inn offers hands-on farm activities and resort amenities. Farm activities include milking the cow and goat, patting the bunnies, collecting chicken eggs, making butter, campfire with marshmallows, horseback riding, and wagon rides. Resort amenities include a children’s recreation program, swimming in the indoor or outdoor pools, boating on the pond, tennis, basketball, shuffleboard, hiking Gap Mountain or Mt. Monadnock, cross country skiing, ice skating, sledding, and snowshoeing, are also available for our guests.

And it is time to relax; three meals are included with every overnight stay. All of their delicious meals are home-cooked and served family-style; you can eat as much as your belly will hold! They also offer vegetarian options and can accommodate special diets upon request. The bottomless cookie jar is, for obvious reasons, popular with guests. We also love that The Inn hosts family vacations, family reunions, meetings and conferences, and holiday gatherings.

Long Island

An iconic destination at any point in the year, Long Island especially comes to life in the fall. Between the many family-friendly wineries and breweries like Baiting Hollow Farm Vineyard and Six Harbor Brewing Company, and the abundance of farms and orchards like Wickham’s Fruit Farm and Woodside Orchards, you’re guaranteed an adventure! We recommend going apple or pumpkin picking at one of the many farms, checking out a museum (the Vanderbilt Museum and Planetarium or the New York Marine Rescue Center are our top picks!) and you certainly can’t forget to attend a fun fall event! Harbes Orchard has an Apple Harvest on September 11-12 and a Pumpkin Harvest on September 25-26. You also don’t want to miss the Long Island Fall Festival in Huntington on October 8-11.

If you’re looking to really dive into the nature of our surroundings, we have some recommendations for that, too: Caleb Smith State Park Preserve has 543 acres of woodlands with marked trails and amazing views. Sunken Meadow State Park is perfect for hiking, biking, horseback riding, and picnicking. While the Bayard Cutting Arboretum in Oakdale has 690 acres of lawns, open meadows, and a wildflower garden for the best Instagram photos.

Putnam County

Mark your calendars for some fall fun in Putnam County, just about an hour away from NYC. We love the Brewster Fall Festival, an annual arts, culture, street vendor, and performance extravaganza, coming up on September 19, 11am-4pm. You can totally plan a day trip to join the family fun and support a good cause at the same time: this year, the festival will have a silent auction to raise funds for restoring the Old Town Hall Theatre. Also happening on September 25 is the Modern Makers Market, a free pop-up event with artisanal goods, glass making and pottery. If you’re aiming for October, then plan for Oktober Fest at Tilly Forest Farm, October 23-24. There will be beer, food, entertainment and more! Don’t feel like committing to a date? Visit Putnam County anytime in the fall for fun at the park, nature walks and museums.

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Manhattan Mandarin

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Polaris Productions Theater Camp

<p>Kids will learn, rehearse, and perform the wonderful Maurice Sendak and Carole King musical, Really Rosie. For 10 weekdays, campers will take part in physical and vocal warm-ups and learn choreography, staging, and vocal parts. They’ll develop skills in acting, singing, character development, and more. This camp will ignite your child’s imagination and passion for performing, build their self-esteem, and help them form lasting friendships. They’ll have fun! At camp’s end, the kids will perform Really Rosie for family members and friends. Kids of all levels of experience, ages 8 through 13, are welcome to join.</p>