Whether you're experiencing it from the water or land, this is a must-see in Boston. You can't beat the skyline views and the walk/biking path makes it accessible for strollers. Bring a picnic lunch or dinner and enjoy all the people watching! Bonus points if you go from mid-April to early May and catch the gorgeous Cherry Blossoms!
Avid hikers, this is a must-see spot! Outside of Worcester is Purgatory Chasm, a hike through a huge chasm with gorgeous views and climbing for days. My big kids (4 and 7) can navigate this trail without help, but with a watchful eye. *Not stroller friendly*
If you're looking for Boston skyline views, cobblestone streets, and a park-like atmosphere, Fan Pier Park has it all. Grab a glass of wine at one of the wine bars and enjoy the sunset.
Chestnut Hill Farm has easy hiking trails for young kids and is stroller friendly with a gorgeous farm atmosphere. Bonus, there are goats to look at while you walk!
If you've been a tourist in Boston, you've probably been to the Aquarium. Next time, try making the Seaport itself your destination. Have kids? Bring a change of clothes and spend time playing in the fountain!
Wingaersheek Beach in Gloucester is our family favorite. From beautiful sunsets to white sand, to amazing climbing rocks...how can you go wrong? If you're planning a weekend trip in-season, GO EARLY, as the parking does fill up!
Castle Island is one of those spots I love to visit mid-week or off-season. While the crowds can be rough on the weekends, it's a great location for a day trip. The paved path around the fort makes easy access for bikes, wheelchairs, and strollers. The historical site, playground, and beachfront offer plenty to fill a few hours.
Callahan State Park is great for dog-owners, those with small kids, or anyone who wants some relatively easy trails. It's great for sledding in the winter, and the pipeline trail is perfect for bikes and strollers.
When you live in Massachusetts, you have to take advantage of all the cool historical sites. The Bunker Hill Monument is a great spot for a picnic and to take in the Charlestown sites.
Nothing makes you feel quite like you've escaped the city atmosphere like a Parisian-inspired romp through lavender fields! Check out one of the many events at Summitwynds during Lavender season.
Bird lovers and hikers will love this spot. Not only do birds eat from your hand (bring black sunflower seeds with you!) but the hikes are breathtaking. Our favorite trail is The Rockery (not stroller friendly).
Bancroft's Castle in Groton was a favorite among my castle lovers. It's a steep climb to the top of the hill but the magical castle ruins make it all worth it. Pack a picnic lunch and enjoy the views from the top!