Southborough

Day Trips

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

day 1
Exploring Southborough
morning
:

Start your day with breakfast at a local café, enjoying fresh pastries and coffee. Afterward, take a stroll around the beautiful Southborough Town Common.

afternoon
:

Visit the Southborough Historical Society to learn about the town's rich history. Pack a picnic and relax at the scenic Fayville Park.

evening
:

Dine at a nearby restaurant offering gourmet farm-to-table options. Wind down your day with a leisurely walk under the stars at one of the local parks.

day 2
Nature Adventure
morning
:

Wake up early and head to Hopkinton State Park for a morning hike. Enjoy the tranquility of nature while immersing yourself in the stunning landscapes.

afternoon
:

Enjoy lunch at a picnic spot in the park and then take a kayak or canoe out on the water. Spend the afternoon soaking in the natural beauty and exploring the surroundings.

evening
:

Return to Southborough for an outdoor BBQ at a local gathering spot. Share stories with friends as the sun sets, creating a memorable evening.

day 3
Autumn Colors
morning
:

Start your day with a walk through the scenic trails to admire the fall foliage. Grab a warm drink from a local coffee shop to enjoy as you explore.

afternoon
:

Visit local farms to pick apples or pumpkins and participate in seasonal activities. The fresh air and beautiful scenery make for a perfect afternoon.

evening
:

Attend a local fall festival that features crafts and food booths. End the night by toasting marshmallows around a campfire with friends.

day 4
Historical Journey
morning
:

Visit the Southborough Historical Museum for a fascinating insight into the town's past. Join a guided tour to get the most out of your visit.

afternoon
:

Explore the historic sites around the town and take photos of the charming architecture. Stop by a local café for lunch to refuel for the rest of the day.

evening
:

Cap off your historical adventure with a visit to a local pub. Relish in the warm atmosphere and perhaps enjoy some live music.

day 5
Arts and Culture
morning
:

Kickstart your day with a visit to the nearby art gallery showcasing local artists. Enjoy a leisurely breakfast at a brunch spot while reviewing the exhibits.

afternoon
:

Participate in a pottery or painting workshop to unleash your creative side. Attend a local theater performance for an immersive cultural experience afterward.

evening
:

Dinner can be enjoyed at a bistro featuring locally inspired cuisine. Reflect on your artistic day over a delicious dessert and coffee.

day 6
Outdoor Family Fun
morning
:

Gather your family for a fun-filled morning at Southborough's parks. Pack some breakfast snacks and explore the playgrounds and open fields.

afternoon
:

Take part in outdoor sports or games at a local sports field. Competitions such as soccer or frisbee can keep everyone engaged.

evening
:

End your family day with a fun pizza outing at a local restaurant. Share your favorite moments over a delightful meal.

day 7
Cycling Southborough
morning
:

Rent a bike and venture out on the scenic trails that weave through Southborough. Enjoy the fresh air and beautiful scenery while getting in some exercise.

afternoon
:

Stop at a local café for lunch and then continue your ride through other nearby trails. Explore new routes and hidden gems in the area.

evening
:

Finish your cycling adventure with dinner at a quaint restaurant featuring seasonal dishes. Reflect on your day while enjoying a relaxed atmosphere.

day 8
Sunset Views
morning
:

Take the morning to relax and have a leisurely breakfast at home or a local spot. Opt for a slower pace and enjoy some quiet time.

afternoon
:

Spend your afternoon hiking to popular lookout points that offer stunning views. Take lots of pictures to capture the experience.

evening
:

Find a great spot for viewing the sunset and enjoy a serene picnic. This memorable scene will be the perfect end to your day.

day 9
Shopping Spree
morning
:

Head to Southborough's local shops for some retail therapy. Browse unique boutiques and find some one-of-a-kind items.

afternoon
:

Stop by a local café to recharge with lunch before heading back for more shopping. Explore any remaining stores on your list.

evening
:

Treat yourself to an upscale dinner at a popular restaurant. Celebrate your finds and enjoy a night of relaxation.

day 10
Community Celebration
morning
:

Attend a community event or farmers' market to experience local culture. Enjoy freshly prepared breakfast options and enjoy the lively atmosphere.

afternoon
:

Participate in various community activities or workshops happening throughout the town. Connect with locals and enjoy what Southborough has to offer.

evening
:

Conclude your day by joining neighborhood gatherings or outdoor movie nights. Enjoy some time with friends and family in a festive setting.

Discover Southborough

Read more in our Southborough 2024 Travel Guide.

Southborough Travel Guide