Ready to Drive For a Few Hours to Somewhere Fun? Here are a Few Road Trip Ideas!

Lugging kids in tow to an airport can be a hassle, and an easier alternative is often times a road trip. The possibilities are endless of where to go when the car is loaded up.

All you need to do is load up your car with gas, travel bags, the appropriate gear for your destination (like sand toys or camping supplies), and of course the family. With a toddler, this is a new skill for me, but it is important to pack activities for the car ride. I am slowly learning that a road trip takes longer with kids, so be prepared to stop more often than you expect. Packing snacks and activities for the car ride is one way to lessen the number of stops along the way.

The one thing to remember about family road trips is keeping the kids entertained, with the endless “are we there yet” or “I have to pee” comments. With enough activity books, fidgets, Yoto or Tonie Box players, or the tablet you will be all set for a few hours of fun on the way to an even more fun destination. But once the gas is in the car and the kid(s) are loaded up in the back, you might be wondering where should I go on my long weekend away.

When you live in the New England region of the US, there are so many different routes you can take with the little ones. When there is a weekend with no plans, my husband and I love to get the kid in the car and just drive. Our favorite destinations are places like Narragansett, Ogunquit, and Old Orchard Beach.

New England is a big region – there’s Vermont, Connecticut (CT), Rhode Island, New Hampshire (NH), and Maine all within driving distance of Massachusetts (MA. In all these road trip suggestions, the starting point will be Boston and its surrounding suburb towns. This will be the first of a 2 part blog post, with part 2 being about road trips south or west of Boston.

First let’s go North of Boston, where the most immediate states surrounding MA are Vermont and New Hampshire. New Hampshire has a few kid friendly attractions, most notably the White Mountains. The White Mountains are where you will find Santa’s Village, Story Land, Living Shores Aquarium, and the Mount Washington Cog Railway taking you up Mount Washington.

Just visiting the Mount Washington North Conway region and Santa’s Village, one could spend about 3 days on this road trip. Mount Washington Cog Railway, Story Land, and the Living Shores Aquarium are all within the same area of each other so can be done in 1-2 days depending on how much time you have. Story Land is a great kiddie amusement park for ages 1-6, right next to the Living Shores Aquarium. In the Living Shores Aquarium, kids and their grown ups alike can see birds and different ocean creatrues as seen in the pictures below. Here is the link to get tickets to the Living Shores and Story Land: https://www.storylandnh.com/

The first time I went up Mount Washington was pre baby, and it was a car ride up the mountain. On my next visit, I’d much rather do this historic train ride. Mount Washington Cog Railway is on my to to visit list on a future trip to New Hampshire’s Mount Washington, but is a must see attraction for kids – especially kids that love trains. Kids that love history, or anything that that moves will enjoy this train ride up Mount Washington that operates all year round. Tickets are $40 for children 4-12 and $54 for adults. Here is the link to learn more: https://www.thecog.com/

Santa’s Village is about 35 minutes north of the base of Mount Washington, so it is better to do that drive on a separate day. In the example map below, the road trip starts in the Boston area around Dedham MA.

https://maps.app.goo.gl/kk94egTj28V9SXdRA

Here are a few pictures from summer 2023 in North Conway, NH.

Another easy but bit longer of a drive from the Greater Boston Area is Vermont. If you are one who loves being out in nature or camping, Vermont is the perfect place to visit for a weekend getaway with the family. A great part of Vermont to visit with the kids is Stowe.

Stowe is a picturesque town with shops, Ben & Jerry’s ice cream, and The Sound of Music’s Von Trapp Family. About 3 1/2 hours north of the immediate Boston area, add an hour for the typical stops that comes when traveling with kids, and you will be surrounded by rolling green hills.

A trip to Stowe can be anywhere from 3-4 days, depending on the time of the year. One full day can be spent at the Ben & Jerry’s Factory tour in Waterbury (pictured below) then exploring the shops in Stowe, and then another day or two can be spent exploring the outdoors. The snowy, cold winter months are a busy time for skiing or snowboarding in the Stowe area. However, if you are like me and prefer the flat trails for walks, there is lots to do outdoors in the warmer weather season as well.

Other than your typical ski lodges, there are two family friendly resorts in Stowe: The Lodge at Spruce Peak and Von Trapp Family Lodge & Resort. Both resorts have amenities including restaurants, pools, and activities for kids. These two resorts can both be booked through Memories With Mill to the best deal, from suppliers such as Expedia or Apple Vacations or Funjet.

For lodging in Stowe, I personally have stayed at the Von Trapp Family Lodge & Resort and would highly recommend this hotel. When you drive up onto the property, you may have to blink twice and remind yourself that this is America and not Austria. From the food to the architecture, the whole resort is inspired by the Von Trapp family’s Austrian heritage. Walking around the property, a guest will find hiking trails, a bakery that makes fresh goodies onsite daily, an indoor pool, an outdoor pool, a brewery & restaurant at the brewhouse, along with guided tours of the family behind The Sound of Music. All activities are included in the lodging fee, which includes tours such as the Sugar Maple Tour or a Meet The Cows walking agricultural tour. If you are a huge Sound of Music fan like travel expert Peggy, then maybe you might get lucky and meet one of the grandchildren of Maria & Captain Von Trapp when you stay at the Von Trapp Family Lodge.

The Lodge at Spruce Peak is a Destination Resort by Hyatt is another great family friendly resort, although a bit more pricey than the Von Trapp Family Lodge. This resort has 4 restaurants, a large outdoor pool, large family size rooms, ropes course, golfing, hiking trails, fitness studio including classes like yoga or pilates, an on-site spa, and a playground. A picture below is from Expedia of the resort.

For driving distance, here is an example with the starting point being the town of Norwood (about 20-30 min outside of Boston): https://maps.app.goo.gl/WhhpSwbBsCx3GiVS9

Want to go north of Boston, but in another direction? Why not visit the Southern coast of Maine? There are lots of family friendly things to do in York, Ogunquit, and Old Orchard Beach – all beach towns just south of the city Portland. Peggy is a huge fan of visiting Maine, so stay tuned for another blog post on choosing hotel lodging for a beach getaway in Maine. For now, let’s highlight some of the most kid friendly activities to do on a weekend trip to Maine.

At the NH border, there are the Kittery Outlets – a fun afternoon or morning of shopping on your way to the destination. Up Route 1 a bit is York, Maine. York has quite a few kid friendly attractions including Nubble Lighthouse, York’s Wild Kingdom, and Fun-O-Rama video arcade on the Short Sands Beach pier. Nubble Lighthouse is a must see attraction in York, where (with close supervision of course) kids can walk on the rocks and families can get pictures with the lighthouse. After visiting Nubble, stop by Dunne’s Ice Cream with the kids for a tasty menu of both soft serve and hard ice cream. Pictured below is Nubble Lighthouse at Sohier Park in York.

When you relax on Short Sands Beach, consider playing fun arcade games at Fun-O-Rama. It is still on my to visit list on one of my next trips to Maine, but from the reviews on Trip Advisor this is your classic old school beachfront arcade. York’s Wild Kingdom is right off of Route 1, and is full of rides and zoo animals for an afternoon or even a day of family time together. York’s Wild Kingdom is only open during the summer months.

The next town up from York is Ogunquit. In Ogunquit, there are two kid friendly activities: the Finestkind boat tours and walking the Marginal Way. Finestkind Cruises offers lobster tours, Nubble Lighthousse tours, as well as breakfast cruises. Most recently, I went on the lobster tour and highly recommend it for kids of all ages. Finestkind cruises: https://www.finestkindcruises.com/

The Marginal Way is a little over a mile long walking path along the coast in Ogunquit, very stroller friendly with lots of benches for those tired little legs. If your traveling companions are anything like my little guy, I am sure they love anything with wheels. After walking along the Marginal Way, take a quick drive up to Kennebunkport and see the Seashore Trolley Museum. If you take a peek at the Seashore Trolley Museum’s event calendar, there may even be a story time for the little ones!

To learn more, check out the Seashore Trolley Museum’s website: https://trolleymuseum.org/

Thanks for reading. If any of these ideas sound fun, be sure to reach out to Peggy for more travel tips. She will happily book your next hotel stay for you to find you the best lodging for your family’s needs. Here’s hoping that you create family memories on your next family road trip!


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