Holliston

Day Trips

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

day 1
Exploring Historic Center
morning
:

Start your day with a visit to the Holliston Historical Society, where you can learn about the town's rich history and its role in the American Revolution. Walk through the charming streets lined with colonial-era homes, enjoying the picturesque architecture and vibrant fall foliage. Don't forget to grab a coffee at a local café, soaking in the morning atmosphere.

afternoon
:

In the afternoon, head to the Holliston Town Forest for a leisurely hike through its scenic trails. The forest is home to diverse wildlife, and you might spot deer or various bird species along the way. After your hike, indulge in a delicious lunch at a nearby restaurant, sampling some of the local cuisine.

evening
:

As the sun sets, take a stroll along the scenic shores of Lake Winthrop, where the tranquil water reflects the vibrant colors of the sky. Enjoy a picnic dinner on the lakeside, with fresh produce and local delicacies you picked up earlier in the day. End your evening with a cozy bonfire, sharing stories as the stars twinkle above.

day 2
Artisan Markets and Local Crafts
morning
:

Begin your day at the Holliston Farmers' Market, where local vendors showcase fresh produce, homemade goods, and artisan crafts. Take your time to explore the various stalls, sampling baked goods and picking up some unique souvenirs. The friendly atmosphere and community spirit make it a delightful way to start your day.

afternoon
:

After the market, visit local artisan shops where you can watch craftsmen at work, such as potters and woodworkers. Engage with the artisans to learn about their techniques and the stories behind their creations. Enjoy a leisurely lunch at a quaint bistro, surrounded by the charm of Holliston's downtown.

evening
:

In the evening, participate in a pottery class at a local studio, where you can create your own masterpiece to take home. The experience is both relaxing and rewarding, allowing you to tap into your creative side. Afterward, enjoy dinner at a farm-to-table restaurant, savoring the flavors of the region.

day 3
Nature and Outdoor Adventures
morning
:

Kick off your adventure with a morning bike ride along the scenic rail trail that winds through Holliston. The crisp morning air will invigorate you as you pedal past beautiful landscapes and lush greenery. Stop at one of the many parks along the way for a quick break and some fresh fruit.

afternoon
:

In the afternoon, head to the nearby Ashland State Park for kayaking or canoeing on the serene waters. You can rent a kayak or bring your own and explore the peaceful surroundings, keeping an eye out for local wildlife. After some time on the water, enjoy a packed lunch at one of the picnic areas in the park.

evening
:

As dusk approaches, return to Holliston and unwind with a nature walk at the Metacomet-Monadnock Trail. The tranquil setting is perfect for reflection and enjoying the beauty of the outdoors. Conclude your day with a casual dinner at a local pub, sharing your day's adventures with fellow travelers.

day 4
Cultural Immersion and Local History
morning
:

Start your cultural immersion at the Holliston Historical Society, where you can explore exhibits and learn about the town's fascinating past. The museum offers a glimpse into the lives of the early settlers and the evolution of the area over the years. After your visit, take a guided walking tour of historic landmarks in the town center.

afternoon
:

In the afternoon, visit the nearby Franklin State Forest to enjoy its hiking trails and beautiful scenery. The forest offers a perfect backdrop for a picnic lunch amidst nature, allowing you to recharge for the rest of the day. Keep an eye out for historical markers that tell the stories of the land and its significance.

evening
:

As evening falls, attend a local theater performance at the Holliston High School auditorium, where you can experience the community's artistic talents. The vibrant performances will surely entertain you and give you insight into the local culture. Afterward, indulge in dinner at a family-owned restaurant, celebrating the flavors of the region.

day 5
Community Fun and Festivals
morning
:

If your visit coincides with a local festival, start your morning with the excitement of community celebrations filled with music, food, and fun activities. Explore various booths showcasing local crafts and cuisines, mingling with residents and fellow visitors alike. The lively atmosphere will definitely set a joyful tone for your day.

afternoon
:

Continue enjoying the festival in the afternoon, participating in games, live music performances, and workshops. Join in on a dance lesson or craft activity that showcases local traditions and heritage. Make sure to grab a delicious lunch from one of the food trucks offering a taste of local flavors.

evening
:

As the festival winds down, find a cozy spot to enjoy the evening entertainment, which often includes local bands or performances. The community's energy is infectious as everyone dances and celebrates together. Wrap up your day with a leisurely dinner at a local eatery, sharing your favorite festival moments with new friends.

day 6
Exploring Local Cuisine and Breweries
morning
:

Begin your culinary journey with a hearty breakfast at a beloved local diner, where you can savor classic American breakfast dishes made with fresh, local ingredients. Afterward, take a guided food tour that showcases the best eateries in Holliston, learning about the history and culture behind each dish. The tour provides a unique perspective on the town's culinary scene.

afternoon
:

In the afternoon, visit a local brewery for a tour and tasting session, where you can sample a variety of craft beers. The knowledgeable staff will share insights into the brewing process and the unique flavors of their creations. Pair your drinks with a light lunch from a food truck or nearby café that complements the brewery's offerings.

evening
:

As night falls, consider joining a cooking class that focuses on local cuisine, where you can learn how to prepare traditional dishes using seasonal ingredients. The interactive experience is a fun way to meet locals and bond over a shared love of food. Conclude your day with a tasty dinner at a nearby restaurant, enjoying the fruits of your culinary adventures.

day 7
Family Fun at Local Parks
morning
:

Kick off your family-friendly day at the Holliston Town Park, where kids can play on the playground while adults enjoy a morning stroll. The park is well-maintained and offers plenty of space for picnics and outdoor games. Bring along some breakfast treats to enjoy together in the fresh air.

afternoon
:

In the afternoon, head to the nearby Lake Winthrop for a variety of activities such as swimming, fishing, or paddleboarding. The family-friendly atmosphere makes it a great spot for everyone to have fun in the sun. Pack a picnic lunch to enjoy by the water, creating lasting memories with your loved ones.

evening
:

As the day winds down, gather at the park for a family barbecue, where everyone can pitch in to prepare delicious meals. Share stories and laughter as the sun sets, creating a warm and inviting atmosphere. End the evening with a family game night, enjoying quality time together.

day 8
Exploring Nature and Wildlife
morning
:

Start your day with a visit to the Holliston Wildlife Sanctuary, where you can observe various species in their natural habitats. The sanctuary offers well-marked trails that allow for peaceful exploration and birdwatching. Bring along a pair of binoculars to enhance your wildlife viewing experience.

afternoon
:

In the afternoon, join a guided nature walk led by an experienced naturalist who can share fascinating facts about the local ecology. The interactive experience will help deepen your appreciation for the area's flora and fauna. After your walk, enjoy a light lunch at a nearby café, reflecting on the day's discoveries.

evening
:

As night falls, consider attending a stargazing event at a local park, where volunteers set up telescopes to share the wonders of the night sky. The serene environment and knowledgeable guides make for a memorable experience. Wrap up your day with dinner at a cozy restaurant, discussing the celestial sights you witnessed.

day 9
Relaxing at Local Spas and Wellness Centers
morning
:

Begin your day with a rejuvenating yoga session at a local wellness center, setting a peaceful tone for the day ahead. The calming atmosphere and experienced instructors will help you connect with your body and mind. Afterward, enjoy a healthy breakfast at a nearby café that focuses on fresh, organic ingredients.

afternoon
:

In the afternoon, pamper yourself with a spa treatment, such as a massage or facial, at one of Holliston's renowned wellness spas. The tranquil setting and skilled therapists will leave you feeling relaxed and refreshed. Take some time afterward to enjoy the spa's amenities, like a sauna or relaxation room.

evening
:

As the day comes to a close, indulge in a nutritious dinner at a health-focused restaurant that emphasizes locally sourced ingredients. The calming ambiance will allow you to reflect on your self-care day. Finish your evening with a peaceful walk in the neighborhood, appreciating the tranquility of Holliston.

Discover Holliston

Read more in our Holliston 2025 Travel Guide.

Holliston Travel Guide