Brookline

Day Trips

Make the most of your day with our curated plans, packed with Brookline's hidden gems and unique experiences!

day 1
Explore Coolidge Corner
morning
:

Start your day with a visit to the Coolidge Corner Theatre for an indie film screening. Enjoy breakfast at a local cafรฉ with fresh pastries and coffee.

afternoon
:

Spend your afternoon exploring the shops on Harvard Street, finding unique gifts and local crafts. Don't forget to grab a bite at one of the many eateries offering diverse cuisines.

evening
:

Wrap up the day with a leisurely stroll in the nearby Beacon Street area. Dine at a local restaurant known for its delicious dinner specials.

day 2
Stroll Through Larz Anderson Park
morning
:

Begin your morning with a refreshing walk through Larz Anderson Park. Enjoy the greenery and beautiful landscapes while taking in the fresh air.

afternoon
:

In the afternoon, picnic in the park or visit the Larz Anderson Auto Museum. The museum showcases antique cars and offers an interesting glimpse into automotive history.

evening
:

As evening approaches, watch the sunset from the park's lookout point. Consider dining at a nearby restaurant that offers outdoor seating.

day 3
Art and Culture in Brookline
morning
:

Visit the Brookline Arts Center to explore local art exhibitions and workshops. Spend time engaging with the creative community.

afternoon
:

Take a guided tour of the historic sites in Brookline, including the birthplace of John F. Kennedy. Enjoy a lunch break in one of the tea houses nearby.

evening
:

Attend a local performance at the Brookline Village Theatre for an evening of culture. Finish off the night with dessert at a nearby ice cream shop.

day 4
Nature Walk at Jamaica Pond
morning
:

Start your morning with a serene walk around Jamaica Pond. Enjoy the views and perhaps spot some local wildlife.

afternoon
:

Have lunch at a cafรฉ along the pond, soaking in the relaxing atmosphere. Venture out for a canoe or kayak rental to explore the water.

evening
:

As dusk settles, enjoy a peaceful picnic by the pond. Later, consider a cozy dinner at a restaurant known for its family-friendly vibe.

day 5
Biking Around Brookline
morning
:

Rent a bike to explore Brookline's scenic bike paths. Pedal through the beautiful neighborhoods and parks to warm up your day.

afternoon
:

Pack a lunch to enjoy at one of the community parks during your biking tour. Visit landmarks along the way to learn about Brookline's history.

evening
:

Return your bike and unwind at a casual eatery for dinner. Share stories of your biking adventures over a hearty meal.

day 6
History Immersion
morning
:

Visit the John F. Kennedy National Historic Site to learn about the Kennedy family's legacy. The guided tours provide fascinating insights.

afternoon
:

In the afternoon, head over to the Brookline Historical Society and explore local exhibits. Enjoy lunch at a historical diner to complete the experience.

evening
:

Join a guided ghost tour of Brookline for a fun and spooky evening. Afterward, grab a warm cup of coffee at a nearby cafรฉ.

day 7
Culinary Tour
morning
:

Start your culinary adventure with a breakfast food tour sampling local favorites. Savor every flavor as you discover Brookline's food scene.

afternoon
:

Continue your tasting journey in the afternoon with visits to local markets and specialty shops. Enjoy a lunch of freshly prepared, local dishes.

evening
:

Join a cooking class to learn how to prepare a Brookline-inspired dish for dinner. Enjoy the meal you've created, reflecting on the day's flavors.

day 8
Music and Relaxation
morning
:

Visit a local coffee shop that features live music in the mornings. Enjoy a warm drink while listening to local artists.

afternoon
:

In the afternoon, head to a nearby park for a music performance or community event. Pack a light lunch to enjoy while soaking in the atmosphere.

evening
:

Attend a concert at a local venue to experience Brookline's vibrant music scene. Afterward, grab dinner at a restaurant with live jazz.

day 9
Stargazing at the Observatory
morning
:

Start your day at the Boston University Observatory for a morning of learning about the universe. Participate in workshops and discussions with astronomy enthusiasts.

afternoon
:

Explore the nearby Fenway area for lunch, sampling various global cuisines. Take some time to relax in a local park and enjoy your surroundings.

evening
:

As night falls, return to the observatory for a stargazing session. Be prepared with snacks for a fulfilling evening under the stars.

Discover Brookline

Read more in our Brookline 2024 Travel Guide.

Brookline Travel Guide