Fun Things to Do Outside of Boston for Couples of All Ages

Looking for something new and exciting to do for a date outside Boston? Whether you want to admire some art or explore the outdoors, there’s no shortage of novel experiences to enjoy with your loved one! 

Boston’s surrounds are filled with myriad opportunities – and we would know. Running day trips near Boston, our team at Keolis massAdventures are Massachusetts locals who know the area like the back of our hand!

We’ve put together our suggestions and personal favorites for some fun things to do near Boston for couples of all ages.

Take a Stroll in Middlesex Fells Reservation

Just a 30-minute train ride from Boston, the Middlesex Fells Reservation is the idyllic place for a romantic stroll – or a fun hike! With over 100 miles of trails to choose from, you and your partner can go on a quick walk or challenge yourselves to a more active experience.

The Long Pond Nature Trail offers a pleasant and easy walk of just 0.9 miles, perfect to do at sunset. If you have dogs, you can take them off-leash at Sheepfold Meadow for a pet-friendly affair. Should you want to do a longer trek, we can recommend our guided hike from Sheepfold to Wright’s Tower at Middlesex Fells. This trail is around 4 miles long and takes 2.5 hours to complete, taking you to the top of Wright’s Tower for panoramic views. You’ll definitely want to bring a camera to snap some photos of you and your beau with Boston in the background!

Have a Picnic on Castle Hill

Overlooking Ipswich Bay, Castle Hill is one of the most picturesque spots outside of Boston. Located on the historic Crane Estate, it offers 165-acres of walking paths, gardens, and lawns to explore. One of the best ways of experiencing this unique destination in Boston is by bringing a picnic to enjoy, sitting between the ocean and the Great House. 

You can take a walk in the Italian Garden and the Rose Garden and admire the perfectly manicured floral displays, or even take a tour of the Great House. Built in the 1920s, this home is a beautiful example of Stuart architecture. With Keolis massAdventures, you can enjoy an easy excursion with our Guided Tour of Historic Castle Hill on the Crane Estate, with your train and tour ticket already included!

Crane Estate

Visit the Worcester Art Museum

If the weather is bad, the Worcester Art Museum is the perfect place for a date outside of Boston. Since its opening in 1898, the museum has amassed a collection of nearly 40,000 objects. With exhibitions ranging from ancient to modern art, you can admire a range of paintings, sculptures, and even armor. 

Grab a bite to eat in the beautiful Renaissance Court, where you can admire the spectacular Byzantine mosaic on the floor dating back to the sixth century. For an in-depth explanation of the exhibits and artworks, you can join a guided tour. Don’t miss the Medieval Chapter House, a 12th-century priory that was rebuilt inside the museum and offers peace and seclusion. 

Go on a Boat Ride on Lake Cochituate

Spend a day at Lake Cochituate, where you’ll have over 600 acres of tranquil waters to sail along. You can rent a boat from Boating in Boston, choosing anything from canoes and kayaks to rowboats and pedal boats. Hop into the same vessel together or sail alongside each other. While you could spend hours paddling along the lake, inland beach areas offer scenic rest points where you can have a snack or go for a swim. Just a 1.5-hour train ride out of Boston, a trip to Lake Conchituate offers an excellent day out for the active couple!

For more ideas on what to do in the area, check out our blog on the Best Way to Spend a Sunny Day Near Boston

Explore the New England Botanic Garden

Nothing quite says romance like being surrounded by hundreds of flowers. At the New England Botanic Garden, you and your loved one can stroll along floral-adorned pathways and discover an abundance of beauty. Smell the natural perfumes and touch the delicate leaves of plants in the court garden, designed to offer a sensory experience. See how nature takes over in the inner park, which has been left to grow naturally. Come spring, you won’t want to miss the field of daffodils. Admire over 25,000 blooming bulbs come to life, creating a spectacle of yellow!

Let Keolis massAdventures take care of your excursion with our New England Botanic Garden Guided Tour, which includes railway tickets to the garden as well as a 45-minute guided tour of the gardens. 

Discover More Near Boston 

With so many more things to experience outside of Boston, we can take you on exciting day trips such as a DeCordova Park Sculpture Tour or even a classic New England Oyster Shucking Experience. There are abundant adventures for you and your partner to embark on, which are all easily accessible with Keolis massAdventures! Feel free to contact us about our tour and day trips outside the city, designed to connect Bostonians and tourists alike with the great outdoors in Massachusetts!

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