Memorial Day Weekend is basically the soft launch of summer, and if you play it right, it can feel like a real getaway.
But, between the pressure to make the most of it and the sheer number of โwhat if we justโฆโ, it can start to feel like a part-time job.
Beach? Amusement park? A quick overnight somewhere? Suddenly, youโre 27 tabs deep, half planning and half hoping it just sorts itself out.
Thatโs where this list comes in.
Eight Memorial Day Weekend options that pass the vibe checkโฆfun, flexible, and family-friendly without being a logistical nightmare.
Weโre talking two resorts, two amusement parks, two easy day trips, and two standout events.
Choose one or mix and match. Either way, youโll head into summer already winning.
Family Resorts That Bring the Summer Vibes
Looking for a Memorial Day Weekend getaway that takes the pressure off?
These Northeast family resorts make it easy to kick off summer with plenty to do, space to relax, and no need to overplan.
Woodloch Resort
Hawley, PA
Because nothing says long weekend like a water fight you didnโt start.
If you’re hoping to turn Memorial Day Weekend into a full-on family getaway without spending hours figuring out what to do once you get there, Woodloch Resort is it.
With lakefront activities, indoor and outdoor pools, and the option to have all your meals included, Woodloch adds just enough structure to make things easy while the kids stay busy and you donโt have to lift a finger.
Drive time: Around 2 hours from NYC and 3 hours from Philadelphia
Woodloch Resort Location: Hawley, PA (Poconos)
Best for: Ages 3โ14 (but older teens will still have a blast)
Why Woodloch Resort works for MDW: Rain? Go bowling. Sun? Head to the lake. Everythingโs walkable and scheduled, so you donโt have to plan a thing.
Whatโs included at Woodloch Resort: All meals, lodging, + activities, with family-style dining and flexible menus for picky eaters.
TLJ Pro Tip: Rooms with separate sleeping areas for kids go fast. Book early if you want more space.
Check current rates and availability at Woodloch Resort.
Margaritaville Resort Cape Cod
Hyannis, MA
All the splash, zero sunburn.
If youโre looking to ease into summer with pool time, water slides, and zero pressure to plan a thing, Margaritaville Resort Cape Cod is a strong contender.
This newly opened resort on the Cape has a full indoor waterpark (guests get 50% off entry), an outdoor pool for sunny days, and bright, beachy rooms that feel like a vacation the second you walk in.
And, if your kids somehow still have more energy to burn, Wicked Waves Waterpark and the Cape Cod Inflatable Park are just minutes awayโฆ so you can extend the fun without much effort.
Drive time: About 1.5 hours from Boston
Margaritaville Resort Cape Cod Location: Hyannis, MA (Cape Cod)
Best for: Families with kids ages 2โ14 who want pool time and vacation vibes.
Why Margaritaville Cape Cod works for MDW:ย Rain or shine, thereโs water fun waiting at Margaritaville Cape Cod, and if you want to explore beyond the pool, the nearby Cape Cod Childrenโs Museum and Flashback Retro Arcade in Hyannis are easy add-ons for a full weekend win.
Whatโs included at Margaritaville Cape Cod: Access to hotel amenities + discounted waterpark tickets.
TLJ Pro tip: The family suites go fastโฆbook early if you want space to spread out.
Check current rates and availability at Margaritaville Resort Cape Cod.
Memorial Day Weekend Day Trips That Feel Like a Vacation
Not every weekend needs a hotel stay to feel like a real getaway.
These Memorial Day Weekend day trips check all the boxes: walkable towns, kid-friendly attractions, good food, and just enough to make it feel like you went somewhere.
Mystic, CT
The only mutiny is refusing to leave.
Mystic is like a starter pack for New England charm. You can check out the belugas at the aquarium, climb aboard historic ships at the Seaport, walk the drawbridge downtown, and grab pizza or lobster rolls before heading home.
Itโs compact but packed with enough to feel like a real New England adventure, making it the perfect place to spend Memorial Day Weekend.
If you’re starting early, youโll want to know where to get the best breakfast in Mystic… bonus points if thereโs outdoor seating and zero wait.
Drive time: 2.5 hours from NYC, 1.5 from Boston
Best for: Any age…easy with a stroller, fun enough for tweens
Why Mystic, CT works for MDW: Mystic is walkable, open early in the season, and has indoor options if the weather takes a turn.
Whatโs in Mystic, CT: Mystic Aquarium, Seaport Museum, Olde Mistick Village, playgrounds, and food on the waterfront.
TLJ Pro tip: Mystic Drawbridge Ice Cream is worth the line (and bribes for good behavior)
Portsmouth, NH
Proof that a stroll counts as an activity.
Portsmouth, NH, is one of those Memorial Day Weekend day trips that just work. It is charming and historic, walkable, and packed with spots that actually welcome families.
Itโs the kind of place where you can wander, park hop, and let the day unfold.
Drive time: About 1 hour from Boston
Best for: Families who love history and exploring a charming town at their own pace
Why Portsmouth, NH, works for MDW: Portsmouth, NH, is a walkable town along the waterfront with spring flowers and plenty of ways to stay outside.
Whatโs in Portsmouth, NH: The Seacoast Science Center, Prescott Park, Albacore Park, Peirce Island Playground, amazing local eats, and harbor views
TLJ Pro tip: Start with brunch at The Friendly Toast and then head to Peirce Island for a picnic or playground break.
Amusement Parks That Say โItโs Summer Nowโ
Nothing says โMemorial Day Weekendโ like sugar, sunscreen, and mild overstimulation.
These amusement parks in the Northeast bring just the right amount of thrill and enough structure to make it feel like you nailed the plan.
Lake Compounce
Bristol, CT
Guaranteed to wear them out before dinner.
If youโre looking for a Memorial Day Weekend plan that screams summerโs here, this is it.
Lake Compounce has been around since 1846, making it the oldest continuously operating amusement park in the countryโฆand it still knows how to bring the fun.
With over 40 rides and Connecticutโs biggest water park, Lake Compounce delivers real thrills for older kids and is small enough to handle with snack-hungry littles in tow.
And yes, the water park opens Memorial Day Weekend. (brrrrrr)
Drive time: About 2 hours from NYC, 2 hours from Boston
Lake Compounce Location: Bristol, CT
Best for: Ages 4โ15, especially if they like mixing dry rides and water slides.
Why Lake Compounce works for MDW: Youโll get full access to both the park and the water rides, plus the crowds at Lake Compounce are manageable this early in the season.
Whatโs included at Lake Compounce: All rides + water park access with general admission.
TLJ Pro tip: Arrive early and knock out the popular rides before lines pick up mid-afternoon. Want more to do in the area? Hereโs our guide to fun things to do in Connecticut over school breaks… Itโs full of easy wins.
Tickets start at $39.99 online. Check hours and buy in advance at lakecompounce.com.
Dutch Wonderland
Lancaster, PA
First real roller coaster energy.
Dutch Wonderland is a fairy taleโthemed amusement park that is basically a rite of passage for Northeast families.
With pint-sized coasters, gentle rides, costumed characters, and a splash pad made for little legs, itโs the perfect intro to amusement parks for the 2โ10 crowd.
And with Dutch Wonderland’s season officially kicking off Memorial Day Weekend, the timing couldnโt be better.
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If your crew lives for thrills, donโt miss our full list of the most Exciting Things to do in Lancaster… Dutch Wonderland is just the beginning.
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Drive time: About 1.5 hours from Philadelphia and 3 hours from NYC
Dutch Wonderland Location: Lancaster, PA
Best for: Ages 2โ10, especially first-time park-goers.
Why Dutch Wonderland works for MDW: Short lines, shaded park, character meet-and-greets, and just enough water play if itโs warm.
Whatโs included at Dutch Wonderland: Admission covers all rides and splash areas. Parking is not included.
TLJ Pro tip: Buy tickets online to save moneyโฆ and skip the ticket booth line.
Check hours and pricing at dutchwonderland.com.
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Curious about turning this into an overnight adventure? The Cartoon Network Hotel is right next door… like, practically share-a-parking-lot close.
Memorial Day Weekend Events Worth the Detour
Looking for more than just backyard barbecue vibes this Memorial Day Weekend? These high-energy events are the kind of thing youโll be glad you planned ahead for.
Boston Calling Music Festival
Allston, MA
Because live music isnโt just for grown-ups.
I know, I knowโฆ kids at a music festival sounds like a bold choice.
But hear me out; Boston Calling is surprisingly family-friendly.
This annual three-day music festival takes over the Harvard Athletic Complex every Memorial Day Weekend, and itโs way more doable with kids than youโd expect.
Music starts around 2 pm, so you can catch great live sets without pushing bedtime. Youโll see plenty of other families there (yes, even babies in headphones), because kids under 10 get in free.
Thereโs also no shortage of good food, interactive art, and space to hang if the kids need a break between sets.
Drive time: Around 4.5 hours from NYC
Boston Calling Location: Allston, MA (Harvard’s Athletic Complex)
Best for: Music-loving families with older kids or festival-curious toddlers.
Why Boston Calling works for MDW: Boston Calling is a full-on experience that delivers that summer just kicked off feeling in the best way.
Whatโs included at Boston Calling: 1 to 3 day tickets available in either GA or VIP; kids under 10 are free with a ticketed adult.
TLJ Pro tip: Bring ear protection for kids, aim for early sets, and treat it like a daytime adventureโฆnot an all-day marathon. Also, thereโs not much shade in the GA area, but VIP tickets come with tented spots and extra space to chill if you want to upgrade.
Check the lineup and passes at bostoncalling.com.
FourLeaf Air Show
Jones Beach, NY
Bonus points if your kid yells โwhoaโ at the same time you do.
This one’s a Memorial Day Weekend classic for a reason. The FourLeaf Air Show (formerly the Bethpage Air Show) turns Jones Beach into a high-flying spectacle with stunt pilots, skydivers, and the U.S. Air Force Thunderbirds all performing over the ocean.
Itโs loud, thrilling, and surprisingly kid-friendlyโฆespecially for airplane-obsessed little ones.
Itโs also totally free (minus parking, $10), which makes it one of the best high-impact, low-commitment events of the weekend.
Drive time: About 1 hour from NYC
FourLeaf Air Show Location: Jones Beach, NY (Long Island)
Best for: All ages, especially plane-obsessed kids and parents who want a beach day with built-in entertainment.
Why FourLeaf Air Show works for MDW: Kicks off the summer season with big energy and no admission fees.
Whatโs included at FourLeaf Air Show: The air show is free; $10 parking at Jones Beach. If free is the vibe this weekend, weโve got a full list of Free Things to do in Manhattan thatโs actually worth your time.
TLJ Pro tip: Arrive early, bring headphones for sensitive ears, and be prepared to walk if the main lots fill up.
Check event details and timing at fourleafairshow.com.
Quick Recap: Where to Spend Memorial Day Weekend
Whether you’re booking a resort, planning a quick road trip, or just looking for something different to do, these Memorial Day Weekend ideas are all vetted, kid-tested, and fun-approved.
Want a full weekend where someone else handles the schedule? Woodloch Resort makes it easy.
Looking for pool time, beach-town vibes, and zero airport lines? Margaritaville Resort Cape Cod is calling.
Prefer a Memorial Day Weekend day trip that still feels like a real adventure? Mystic, CT or Portsmouth, NH are both worth the drive.
Need a high-energy day without packing an overnight bag? Lake Compounce and Dutch Wonderland deliver.
Want to shake things up and make a core memory? Boston Calling or the FourLeaf Air Show will do the trick.
Want to find the best stops along I-95 between New York City and Boston? This list of roadside stops is sure to make your kids squeal with happiness.
Whatever kind of vibe youโre going for this Memorial Day Weekendโฆlaid-back, all-in, or something in between, thereโs something here thatโll make it feel like summer officially started.
Happy travels…
