Looking for some unique and fun dates in Massachusetts? Even if you’re not planning anything special anytime soon, it’s always a good idea to have a few awesome and romantic suggestions up your sleeve. We’ve gathered a few great date activities and locations that will appeal to everyone, whether your sweetheart is an adrenaline junkie or loves to curl up and get cozy.

1. Beer and batting cages at the Shortstop Bar and Grill
Yelp/Kelsey R.
This is a great, lighthearted, fun thing for couples to do in Massachusetts who enjoy both brews and baseball. The atmosphere here is relaxed, the prices are reasonable and there’s often live music. After you’ve knocked back a few beers, head to the restaurant’s batting cages to loosen up and have a few laughs.
2. Go on a cupcake crawl
Boston Chocolate Tours
This is exactly what it sounds like. Travel to Boston's best cupcake bakeries and see if you've got similar tastes!
3. Head to the aquarium
Facebook/New England Aquarium
The lighting at an aquarium is unexpectedly dreamy – soft blues and shimmering greens make for a unique date ambiance. For a timeless classic date idea in Massachusetts, try the New England Aquarium for the best aquatic experience in the state.
4. Climb to the top of Mount Greylock
Flickr/MOTT
This is probably not a great first date idea (you might not want to be in the middle of the woods with someone you just met), but it's an awesome way for couples to breathe some fresh air into their lungs and relationship. Hike to the top of the tallest peak in Massachusetts and you'll be rewarded with an amazing view and a great opportunity for a romantic photo. You can also drive up to the summit if that's more your style.
5. Go on a ghost tour
Flickr/Corey Balazowich
Science says that facing scary situations helps couples bond, so why not bundle up and head out to hunt some spooks together? If you really want to have a unique date in Massachusetts, you can always gas up the car and take this road trip to Massachusetts' most haunted places.

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6. Go for a scenic bike ride
Tripadvisor/TWKleban
If you both like to cycle, why not take a relaxing ride around the local area? For some truly stellar ocean views while you ride, try the Shining Sea Bikeway on Cape Cod.
7. Browse the stacks at the Brattle Book Shop, and then grab some hot cocoa
Flickr/Bill
This is one of the coolest book shops in the state. Known for its unique outdoor shelves, the Brattle Book Shop also has plenty of interesting tomes indoors for when the weather is chilly. Stop by nearby L.A. Burdick for a cup of rich hot chocolate afterward.
8. Go on a food tour or trail
Boston Chocolate Tours
Chocolate anyone? Boston Chocolate Tours offers a walking tour of the city’s best chocolate shops, complete with samples! If you’re based out west, try the amazing Berkshire Wine and Cheese Trail for a tasty way to spend the day munching and enjoying each other’s company.
9. Head to the roller rink
Roller Kingdom, 355 Middlesex Rd, Tyngsborough, MA 01879, USA
Flickr/Lisa @ Sierra Tierra
You're never too old for this retro date idea. The Roller Kingdom in Tyngsboro is an awesome option for this one. This is a great way to mix things up without getting too crazy. Strap on your skates and start grooving to the music. Speaking of music, there's also karaoke!
10. Explore a new town or city
Flickr/MOTT
Massachusetts is full of hidden gem towns, and what better way to explore one than with your sweetheart? Head into town, browse the shops, and find a cozy restaurant or bar in which to gaze at each other over some tasty fare. There’s nothing like unfamiliar places and new memories to inject a bit of novelty into a relationship. If you need some inspiration, here’s a list of charming small towns in Massachusetts with great dining options.
11. Get in touch with your wild side at Southwick's Zoo
Flickr/MOTT
If you think the aquarium is a great date option, then you'll love the zoo. Meet and greet with exotic animals at the largest zoo in Massachusetts. There are plenty of petting areas where you can interact with the tamer residents of the zoo, like deer and goats. You'll bond with the animals while bonding with your sweetheart.

For more romantic locales in Massachusetts, take a look at the most magical places for a wedding in the state.

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More to Explore

Things To Do In Massachusetts

Jackie Ann | October 03, 2022

What are the best road trips through Massachusetts?

Massachusetts has a lot to offer, and road trips are one of the best ways to see the sights of the Bay State. There are plenty of road trips in Massachusetts you could take, depending on what you have your sights set on. During the summer months, a hidden beach road trip is always a good idea, especially if you want to escape the crowds. Or maybe you want to chase waterfalls and take an epic waterfall road trip through Massachusetts, including majestic cascades like Bear’s Den Falls and Bash Bish Falls. For a truly enchanting drive, consider taking a road trip to some of Massachusetts’ castles. 

What are the best outdoor activities in Massachusetts?

With such a diverse landscape, spending your time outdoors is always a good idea. Since Massachusetts experiences the full spectrum of the seasons, there’s always something beautiful just around the corner, and hitting the hiking trails or spending time walking along a beach are both great Massachusetts date ideas. Hiking doesn’t have to take all day either, there are plenty of short-and-sweet trails in Massachusetts that don’t compromise on scenery but still offer a chance to experience the outdoors. 

What are the most unique places to spend the night in Massachusetts?

Some of the most unique places to spend the night in Massachusetts will showcase just how beautiful the Bay State really is. How does sleeping in a treehouse sound? Or maybe you prefer the wide open space you get when renting a farmhouse on a working farm where you can wake up and enjoy your morning coffee with the view of goats and sheep grazing in your front yard. Of course, if you really want to have some fun, you can always summon your inner wizard and rent this Harry Potter-themed Airbnb in Massachusetts. Expecto sweet dreams!

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