Looking for a fun, low‑pressure way to spend time together in Boston? The Greenway offers countless ways to turn a simple walk, snack, or shared experience into a memorable date. Whether you’re planning something romantic, looking for a casual outing with friends, a solo reset, or a family adventure, The Greenway is your go‑to destination for connection and exploration.
We’ve rounded up some of our favorite date night (and day!) ideas for different times in the year. You can also download our printable guide to save for later or share with someone special.
Date Ideas for Couples
Take a walk through the snow (or sunshine). There’s something undeniably romantic about strolling The Greenway in winter—quiet paths, fresh air, and the city moving a little slower. In warmer months, the same paths offer blooming gardens and lively energy.
Swing on a bench in the North End while enjoying the Winter Lights. Slow things down and enjoy one of The Greenway’s most charming corners. Sometimes the best dates are the ones with nowhere else to be.
Share a picnic on the lawn. Grab a snack from a food truck or local eatery, bring a blanket, and have a picnic under the city skyline!
Family Date Ideas
Go for a ride on the Greenway Carousel. A classic Greenway experience—whimsical, playful, and perfect for embracing your inner kid together. Plus, the Carousel is open for special hours in February! See the full schedule on our website calendar.
Explore The Playway. No matter what the season, The Playway showcases all of the family-friendly attractions on and off The Greenway that bring wonder and excitement to any Boston outing. From interactive public art and delicious food trucks to local attractions like the New England Aquarium and Boston Children’s museum, there is so much to explore!
Grab lunch from a Greenway food truck and have a picnic. Turn a weekday lunch or weekend bite into an easy daytime date with local food trucks vending right on the park!
Date Ideas for Friends
Attend a summer or fall movie night. Bring a blanket, cozy up, and enjoy a movie under the stars during our seasonal programming. In the summer, Coolidge on The Greenway brings a monthly movie to the lawn, and in the fall, our festive movie series provides a cozy and fun evening activity for everyone to enjoy!
Shop the Greenway Artisan Market. Browse handmade goods, local art, and unique finds at our seasonal artisan market – perfect for gift‑giving or just wandering side by side.
Ride the Boston Frostival Ferris Wheel (February 2026 only). Take a spin on the Frostival Ferris Wheel this winter, right next to the Greenway Carousel.
Post‑work drinks at a Greenway Beverage Garden. Meet up after work, unwind outdoors, and let the park set the tone for a relaxed evening.
Solo Date Ideas
Take a self‑guided tour along The Greenway. Learn more about the park’s history, public art, and gardens as you explore at your own pace using our self-guided tour.
Treat yourself to a snack from a food truck. Sometimes dessert is the date.
Take a free fitness class. Some self-care and movement is a wonderful way to spend a morning or afternoon, with our free fitness classes sponsored by Blue Cross Blue Shield of Massachusetts. (The 2026 season will take place from May-October.)
Bring a book and spend an afternoon in the gardens. Take some time to enjoy the sounds of the city and the calm of the park, all while enjoying a good book or a relaxing afternoon.
Save It for Later
Planning a date doesn’t have to be complicated. Download our Date Night on The Greenway Guide for a printable list of ideas you can keep handy all year long.
Whether it’s your first date, a standing weekly tradition, or a spontaneous afternoon, The Greenway is ready to welcome you and your loved ones.