The Best Summer Family Road Trips

Summer Family Road Trips!

We all have memories from our childhood of the trips we took with our family; being kids, we remember only the funny and good stuff. Now that we’re parents, we know that while road trips can be intense, especially with younger kids, this time together bonds us and will be part of the fabric of our children’s memories.

A discovery we may have always known as we make our way out of the pandemic is that New York and the cities and states surrounding our hometown are full of beauty, history, and adventure.

Here is to a summer of awe and travel with these must road trips for Summer 2021.

Catskills, NY

A recent trip my family took was to the Catskills. There were a few things that went through my mind when I visited the Catskills. One, we need to do this more—two, what an easy trip it is. And three, Woah, can the Catskills be even more beautiful? And while New York is reopening and there are many things to do, why I loved our road trip to the Catskills was that it was something we could do even as the world was in a crazy state. Of course, it is always nice to visit places and try the food, but nature alone in the Catskills is a sight. First, we took a hike, literally. There are many hiking trails in the Catskills, and my mom’s tip is to check out the Great Northern Catskills’ website to find the trail that works for your family. While nature is supreme in Greene County, I have a list of what we will be visiting this summer. Top on this list is horseback riding, more hiking trails, food tasting at the restaurants, and taking our oldest son on a camping trip or staying at one of the family resorts. Yay for summer upstate!

Travel Tip: For a family-friendly hike, check out Mountain Top Arboretum, a public garden nestled in the Catskill Mountains where kids can explore native plant communities, natural meadows, wetlands, and of course, hike the forest.

Annapolis, Maryland

Since the pandemic, one sneaky parenting move I have been doing with the kids is picking fun spots to visit that are also full of history. Annapolis is just the ticket. The car ride is about 3.5 hours (starting from Midtown). Go for a long weekend or make it a family vacation and spend the week, as there’s plenty to do. We love to stay downtown at one of their charming beds, breakfasts, historic inns, or hotels. We park the car and explore on foot since Annapolis is a walkable town. First stop, City Dock. We enjoy watching the boats parade along Ego Alley. If your family loves being on the water, take a 40-minute harbor cruise or a sail on the historic skipjack, the Wilma Lee. For fun with the older kids, you can also rent kayaks or stand-up paddle boards. With 533 miles of shoreline, Annapolis and Anne Arundel County offer endless opportunities for on-the-water fun. When it’s time to feed the kids, hop aboard a water taxi for a quick ride to a delish meal along Restaurant Row and visit the Annapolis Maritime Museum and Park; it just reopened with a new state-of-the-art exhibition, Our Changing Waterfront, that the kids adore. Don’t miss the Maryland State House – the oldest in continuous legislative use in the nation; the home of the Declaration of Independence signer William Paca and stop by for a tour of the U.S. Naval Academy! To plan your trip check out!

Travel Tip: Be sure to make time to head over to the Banneker-Douglass Museum of African American history and culture, focusing on the history of Maryland.

Hudson County, NJ

If looking for a day trip or a long weekend getaway with the fam this summer — you’re going to want to check out Hudson County, New Jersey. With education and history (and fun!) being a theme of these road trips, Hudson County (NJ) is on point. For your skater kid, head over to one of the many skate parks (Bayonne, Hoboken, Jersey City, Union City, and West New York) so they can show off their backside moves. There are plenty of gorgeous parks for the little ones — Pier A Hoboken, North Hudson Braddock Park, Hamilton Park Weehawken, to name just a few. My favorite for the entire family is Liberty State Park, situated on the Hudson River. The family (bring the stroller for the wee ones) can walk the two-mile Liberty Walk promenade with views of the One World Trade Center and Battery Park. When it’s time to rest or eat lunch, eat at the Liberty House Restaurant and take in the scene on the waterfront. And bringing that education and history theme into the trip, hop on a ferry via Statue Cruises and visit the Statue of Liberty and Ellis Island. Liberty Science Center, the immersive, hands-on science museum is l. With so much to do in Hudson County, NJ — check out all the attractions, places to eat delicious food at

Travel Tip: If, like me, you appreciate a well-planned map, you’ll love these helpful road trip itinerary maps that can be downloaded. I have my eye on the map that educates and traces New Jersey’s Black Heritage in Northern New Jersey and the Warren Heritage and Western Highlands: New Jersey Scenic Byways, but there are plenty more to choose from. Go to to pick your road map.

Poconos Mountains

(northeast Pennsylvania’s Carbon, Monroe, Pike, and Wayne counties)

If looking for a summer trip in the mountains, a Poconos visit needs to be in your future. This beauty is right out of a fairytale book with non-stop mountain terrain, rivers, waterfalls, and woodlands. While popular in the winter, the summer in Poconos is just as gorgeous and fun. There are 261 miles of bike and hiking trails as well as fishing and boating. Families can also visit the nine state parks and two National Parks. There are many camping options for families to pitch a tent and enjoy the outdoors as well. If kids need a break from nature (yeesh, I know only kids would need a nature break), your youngest kids will love checking out the giraffes at claws n paws or learning about the history of local art at the Antoine Dutot Museum & Gallery. There is so much to do in the Poconos, so definitely check out to map out your family road trip to the Poconos.

Travel Tip:  Want to make more of a commitment to your summer vacation in the Poconos and visit year-round? I can’t blame you. The Sérénité is a private residence club at Camelback Mountain. The Sérénité has created a hybrid vacation program where your new vacation home includes luxe amenities, a clubhouse, and more. Yes, please!

Rockland County, NY

When you live in the city, a road trip can also mean a day trip. And after one crazy year, re-exploring is on the top of so many of our to-do lists this summer. Rockland is only one hour away from the city by car. You can also go by bus in the same amount of time. The first stop you should check out is beautiful Piermont, where I would immediately be happy to move to ASAP and live the rest of my years in this scenic town. Located on the riverside, kids will love the Piermont Piers. You can make an appointment at for a guided tour or sailing lesson in July and August. Although the vibe is a small town, there are amazing restaurants and quaint shopping in Piermont; if looking to engross the family in nature, head over to Harriman State Park, where you’ll find 31 lakes and reservoirs, hiking trails, beaches, and camping sites. For the big kids, walk the new 12-foot wide path at the Governor Mario M. Cuomo bridge. There are six scenic overlooks to take in, and the path is 3.1 miles. And before heading out on your trip check out to see if there is a game on the schedule of The New York Boulders- Rockland’s own American independent professional baseball team!

Travel Tip: Right over the Mario Cuomo Bridge is West Nyack, where the popular Palisades Center can be found. With safety measures in place, this four-level shopping center offers 225 brands all in one spot. I can find all my favorites here (Sephora, Zara, and H&M) as well as my go-to stores for the kids (Target, Vans, and Old Navy), which means hello back to school shopping. And now that Covid restrictions are opening back up, here are some of the activity places now open: 5 Wits, Aim Point, AMC Theatres, Autobahn Indoor Speedway, Billy Beez, Build-A-Bear Workshop, Palisades Center Carousel, Color Me Mine, Palisades Center Ferris Wheel, Game Show Room, Glitter & Glam, Levity Live, Mystery Room, OMG Entertainment, Palisades Ice Rink, Palisades Climb Adventure/Sky Tykes Ropes Course, Space Adventure Glow in the Dark Mini Golf, Spin Zone and opening Soon – Lucky Strike and Exo Drome.

Colonial Williamsburg, Virginia

My husband grew up on road trips, and to this day, we drive all over the country. This summer, we want to focus on the ‘summer slide’ and head over to spots like Colonial Williamsburg. The largest outdoor living museum in the country, the family, through immersive and authentic 18th-century experiences, can learn everything from this time period this summer. Put your mask on and stroll through the unique art museums like the Abby Aldrich Rockefeller Folk Art Museum and The DeWitt Wallace Decorative Arts Museum. Afterward, enjoy lunch at the museum café, explore the garden, take a carriage ride, all while learning about this time in history.

Travel Tip: For more ways to enjoy Colonial Williamsburg, plan your visit, get your tickets, and map out your stay by visiting

Putnam, NY

Road trips are nothing like the movies unless it is the sort of flick where you stop every half hour at a rest stop to use the bathroom a million times. And, yes, the kids need to be entertained 24/7. At an hour and twenty-ish car drive, Putnam County makes for a perfect family trip. As New York reopens, Putnam is a pleasant visit if you seek an area with beautiful nature and plenty to do outdoors. There are gorgeous lakes to visit, such as Lake Canopus in Fahnestock Park, where you can enjoy a picnic lunch and soak up the warm sun. If taking the train, take the metro north train from Grand Central, which will take you right to Brewster, bikes are allowed on the train, and you can start exploring right when you arrive. If looking for activities for your younger kids, check out the self-guided tour (10 am to 4 pm, seven days a week) at Tilly Foster Farm to get a look at the farm animals. After you spend the day running around, there are plenty of delicious food options. From Mexican, Italian, Japanese to a good ole hamburger — there is something for even the pickiest family member.

Travel Tip: For the history buffs in the family, a must-visit is the West Point Foundry Preserve. Check out the first steam engines, locomotives, and pipes used for New York’s water system. There are even cannons from the Civil War and trails that lead to foundry buildings that teach about the Industrial Revolution and Civil War.

Lexington, Massachusetts

If looking for a road trip where you can go on tours every day, Lexington in Massachusetts is a great city to visit. While history buffs will enjoy just walking through this historical town, the tours are an excellent way for the kids to learn about The Battles of Lexington and Concord, the first battles to be fought in the American Revolution. Take a guided one-hour Battle Green tour or self-guided phone tour of Lexington Battle Green and The Old Burying Ground, which dates back to 1690. For a short (35 min) but incredible tour, visit the Buckman Tavern where locals and travelers would gather and have town meetings. Visit for more places to map out your trip!

Travel Tip: A Lexington trip must! Before your visit, check out for the Liberty Ride Trolley Tour which is set to open soon after a pause due to COVID. The Liberty Ride trolley tour is a 1.5 hour guided trolley tour of both Lexington and Concord. Once onboard the Liberty Ride, you’ll again be transported back in time to the 1770s, where you’ll learn about the events that led up to April 19, 1775, and beyond as you travel through Lexington Minuteman National Park and Concord. Upon arrival in Concord, you’ll take a momentary detour into the 1800s to learn about Concord’s famous authors – Emerson, Thoreau, and Alcott. You’ll learn about Paul Revere’s famous midnight ride, visit the spot where he was captured by the British, and so much more.

Rhinebeck, NY

My tip on Rhinebeck? You need to know Rhinebeck. This town was the first road trip I took years before I had kids; I immediately envisioned moving from the city to this fabulous town. Alas, I never did, but I visit the quaint village a few times a year for its excellent shops, tight-knit community, and restaurants.

Visit for the day by car or train and soak in the laid-back vibes of Rhinebeck. If going for a few days or a week, make sure to look into the local Airbnb rentals. Or stay at the quaint The Gables at Rhinebeck Inn or if your family vacation, make it about self-care, and stay the week at the Mirbeau Inn & Spa Rhinebeck. I also love that you can jump into a yoga class at the famous Mirbeau Inn & Spa Rhinebeck while the family checks out the sights. Other must-stops are the Northern Dutchess Botanical Gardens to gawk or shop for some gorgeous plants. Drayton Grant Park at Burger Hill, a 76-acre park where you can see the Hudson River and a majestic view of both the Catskill and Taconic Mountians. Don’t forget the camera!

Travel Tip: Go to the Dutchess County Fair! There is simply no other fair like the Dutchess County Fair. While there will be tweaks due to COVID, the fair is back after understandably canceling last year. Expect to see animals, games, and the food that we all love. Known as the most significant agricultural six-day fair in New York State — this fair is what many New Yorkers and people all over wait all year to visit. It is the greatest if not the most famous fair in the world. Dates: 8/24-8/29, visit for more information.

Relevant Directory Listings

See More

5Photo for Kids

<div class="yj6qo"> <div style="color: #222222; font-family: Arial, Helvetica, sans-serif; font-size: small; background-color: #ffffff; text-align: center;">After-school workshops for kids ages 11 to 17 designed to introduce students to the art of photography and the digital camera as a creative instrument to capture and create dynamic photographs. Students will learn aperture, shutter speed and ISO, photograph outdoors, exploring Brooklyn and beyond, and indoors, shooting table-top set-ups and portraits. Students receive post-production (editing) education, and one of their images framed to take home.</div> <div style="color: #222222; font-family: Arial, Helvetica, sans-serif; font-size: small; background-color: #ffffff; text-align: center;"> </div> <div style="color: #222222; font-family: Arial, Helvetica, sans-serif; font-size: small; background-color: #ffffff; text-align: center;">For more information go to <a style="color: #1155cc;" href="" target="_blank" rel="noopener" data-saferedirecturl=""></a></div> </div>

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>

Manhattan Mandarin

<p>Manhattan Mandarin runs the Mandarin after-school programs at over 40 schools</p> <p>nationwide, including St. Bernard's, Chapin, Allen-Stevenson, and Buckley. Whether</p> <p>in schools, students' homes, in the office, online, or on our beloved China trips, our</p> <p>teachers and tutors have helped hundreds of students of all ages master the Mandarin</p> <p>language on their own unique paths to fluency. Our philosophy has always been to</p> <p>make private lessons and classes perfectly tailored for each individual student. We</p> <p>look forward to working with you.</p> <p>- Jamie Keyte, Founder</p>