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 Center
morning
:

Start your day with a stroll through Southborough Center, where you can admire the quaint historic buildings and enjoy your morning coffee at a local café. Take a moment to visit St. Anne's Church, a beautiful landmark with impressive architecture. Don’t forget to snap some photos of the scenic views.

afternoon
:

After lunch at one of the charming eateries, immerse yourself in local history at the Southborough Historical Society. Visit the Old Burial Ground, which dates back to the 1700s and explore the stories of the town's early settlers. Consider spending the late afternoon walking along the trails of the nearby Sudbury River, soaking in the natural beauty.

evening
:

For dinner, savor a meal at a cozy restaurant that highlights regional cuisine. As the sun sets, relax at the Southborough Town Park, where you can take a leisurely walk or simply enjoy the serene atmosphere. Conclude your day with some stargazing, as Southborough’s minimal light pollution allows for a magnificent view of the night sky.

day 2
Nature and Adventure
morning
:

Kick off the day with a refreshing hike at the nearby Breakneck Hill Conservation Land. Enjoy the scenic trails that meander through lush woodland and offer beautiful vistas. Bring binoculars if you're a birdwatching enthusiast, as the area is home to diverse wildlife.

afternoon
:

Pack a picnic to enjoy at the summit of Breakneck Hill, where the panoramic views will take your breath away. Spend some time relaxing and soaking up the sun while surrounded by nature. After lunch, explore the surrounding trails or engage in some outdoor activities such as mountain biking or geocaching.

evening
:

Return to town and unwind at a local brewery for a tasting of handcrafted beers and a selection of bar bites. Engage with the locals and enjoy the laid-back vibe of the area. As dusk falls, consider catching a live music performance if there's one happening at a nearby venue.

day 3
Arts and Culture
morning
:

Dedicate your morning to appreciating the arts by visiting the Southborough Library, which often features local art exhibits. Spend some time browsing through the collection or attending a workshop if one is scheduled. The library's tranquil environment makes for a perfect start to your day.

afternoon
:

Afterward, head to a nearby art studio or gallery to immerse yourself further in the local art scene. Participate in a hands-on art class or simply enjoy observing talented artists at work. Grab lunch from a nearby café, providing you with the fuel to continue your artistic exploration.

evening
:

End your day with a visit to the Southborough Community Center, where you might find a local theater performance or musical event taking place. Enjoy the sense of community as you socialize with locals and experience the vibrant cultural scene. Wrap up the evening with dessert at a local bakery, indulging in sweet treats to celebrate your artistic day.

day 4
Historical Discoveries
morning
:

Start your day with a visit to the historic Southborough Village, where you can learn about the town's rich history. Tour the impressive Old Town Hall and explore the tales told by the vintage architecture. Take a moment to appreciate the historical significance of each site you encounter.

afternoon
:

After a historical tour, enjoy lunch at a nearby diner that offers a taste of traditional New England fare. Use the afternoon to explore more museums or historical sites, such as the original Southborough Grammar School. Spend time engaging with knowledgeable guides who can provide you with fascinating insights about the town's past.

evening
:

As night falls, return to the Village and enjoy a nice dinner at a family-owned Italian restaurant cherished by locals. The cozy atmosphere and hearty dishes will be the perfect way to end your day immersed in history. If the weather permits, take a leisurely evening walk through the softly lit streets, reflecting on your day of discovery.

day 5
Family Fun Day
morning
:

Begin the day with a visit to the Southborough Recreation Center, where you can participate in fun family activities and games. Whether it's swimming or group sports, the energy will kickstart your family's day. Spend quality time together before lunchtime.

afternoon
:

After a fun-filled morning, head to the Southborough Community Park for a picnic lunch. The children can enjoy the playground while the adults relax on the grass or join in on a family game of frisbee. This outdoor adventure will create wonderful memories for everyone involved.

evening
:

As evening approaches, visit a local pizzeria that caters specifically to families, serving up delicious slices everyone will love. Post-dinner, consider heading back to the Recreation Center for a family-friendly movie night or an organized game tournament. This will be the perfect capstone to a day full of laughter and connection.

day 6
Culinary Exploration
morning
:

Start your culinary tour with breakfast at a local brunch spot known for its farm-to-table options and delicious pastries. Relish the flavors of freshly brewed coffee paired with innovative breakfast dishes. This delectable experience will energize you for the day's culinary adventures.

afternoon
:

After brunch, embark on a guided food tour that introduces you to Southborough's best dining establishments. Sample different cuisines and learn about the local culinary scene from passionate chefs and owners. The afternoon will be filled with delightful flavors and engaging conversations.

evening
:

End your culinary exploration with a fine dining experience at a well-reviewed restaurant featuring an exquisite seasonal menu. Pair your meals with wines selected to enhance your dining experience and enjoy the elegant atmosphere. Feel satisfied at the end of the night as you reflect on the culinary journeys you've undertaken.

day 7
Outdoor Recreation
morning
:

Pick up your hiking gear and head to the nearby conservation lands for an invigorating morning hike. Discover the beauty of the trails and enjoy the fresh air while listening to the sounds of nature. This is an excellent way to recharge before enjoying the rest of the day.

afternoon
:

Post-hike, have lunch at a quaint café, which has large windows showcasing beautiful views of the landscape. Spend your afternoon engaging in outdoor activities such as paddleboarding or kayaking on a nearby lake. These activities will allow you to appreciate Southborough's natural beauty from a different perspective.

evening
:

As the sun sets, enjoy a relaxing evening barbecuing with friends or family at a scenic park. Share stories around a warm fire pit and savor the comforting tastes of grilled favorites under the stars. This peaceful close to the day will leave you with lasting memories of outdoor fun.

day 8
Wellness Retreat
morning
:

Start your wellness journey with a guided yoga session at a local studio surrounded by tranquil nature. Allow the calming atmosphere to rejuvenate your mind and body, followed by light refreshments. This peaceful start will prepare you for a day of relaxation.

afternoon
:

Visit a nearby spa for a series of indulgent treatments, including massages and facials that will melt away your stress. While enjoying your treatments, unwind in relaxation lounges with herbal teas and calming music. This dedicated time for self-care will enhance both your physical and mental well-being.

evening
:

In the evening, enjoy a healthy dinner at a restaurant that focuses on organic and nutritious meals. Spend the time reflecting on your wellness journey and the serenity you’ve experienced throughout the day. Finish the night with meditation or relaxation techniques to cultivate the peace you’ve established.

day 9
Shopping and Exploring Local Markets
morning
:

Start your day exploring the bustling local farmers' market, where you can find fresh produce and artisanal goods made by local vendors. Enjoy sampling delicious treats, from freshly baked goods to homemade jams. This lively scene is a fantastic opportunity to meet local artisans and learn about their crafts.

afternoon
:

After strolling through the market, head to the local boutique shops to discover unique clothing, handcrafted jewelry, and specialty gifts. Spend time chatting with shop owners as you browse their exceptional collections. Enjoy lunch at a charming bistro that captures the essence of Southborough's culinary offerings.

evening
:

Conclude your shopping day with a casual dinner at a favorite local eatery, enjoying the relaxed ambiance. If the timing aligns, catch an evening market that features live music or entertainment. This vibrant conclusion to your day will leave you with a sense of community and pride in local support.

Discover Southborough

Read more in our Southborough 2025 Travel Guide.

Southborough Travel Guide