Westborough

Day Trips

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

day 1
Exploring Downtown Westborough
morning
:

Start your day with a delightful breakfast at a local café, enjoying fresh pastries and aromatic coffee. After your meal, take a leisurely stroll through the charming downtown area, visiting unique shops and boutiques. Don’t forget to capture some photos of the historic architecture that adorns this quaint New England town.

afternoon
:

In the afternoon, immerse yourself in the outdoors by visiting the picturesque Lake Chauncy. Rent a kayak or paddleboard to explore the tranquil waters, or simply relax by the shore. Pack a picnic lunch to enjoy under the shade of the trees while taking in the beautiful scenery.

evening
:

As night falls, dine at one of Westborough's cozy restaurants, where you can savor local dishes made with fresh ingredients. After dinner, take a stroll around the town center to appreciate the twinkling lights and friendly atmosphere. End your evening with a scoop of ice cream from a beloved local ice cream shop.

day 2
Historical Discoveries
morning
:

Begin your day by visiting the Westborough Historical Society to learn about the town's rich history and heritage. Engage with interactive exhibits and explore artifacts that tell the story of the area. This insightful visit sets the stage for understanding the culture of Westborough.

afternoon
:

Spend your afternoon taking a guided tour of the historic properties, such as the Fay School or the Old Town Common. Feel the echoes of the past as you explore buildings that have stood the test of time. Wrap up your day with a visit to a local craftsman or art studio to see the creative community in action.

evening
:

In the evening, attend a community event or concert often hosted at the Westborough Town Hall. Connect with residents and enjoy live music or performances that showcase local talent. Treat yourself to a lovely dinner at a nearby bistro, discussing the day's discoveries.

day 3
Nature’s Retreat
morning
:

Kick off your day with a hike at the Westborough State Forest, where the trails are surrounded by stunning foliage and wildlife. Enjoy the fresh morning air and listen to the sounds of nature as you make your way through the woods. This invigorating morning will energize you for the adventures ahead.

afternoon
:

After your hike, head to the nearby St. Mary's Pond for a peaceful afternoon. Bring your binoculars to observe local bird species or take a nature photography walk. This is a wonderful opportunity to unwind and appreciate the beauty of the local ecosystem.

evening
:

As the sun sets, gather with friends or family for a campfire cookout at one of Westborough's parks. Share stories and enjoy s'mores under the starlit sky while taking in the wonderful ambiance. End your night by playing outdoor games, creating lasting memories of your time in nature.

day 4
Family Fun Day
morning
:

Start your family fun day with a hearty breakfast at home or a local diner that offers kid-friendly favorites. After breakfast, head over to the Westborough Public Library for story hour, where young ones can engage in fun literary activities. This interactive start fosters a love for books and stories.

afternoon
:

After the library, take a trip to the Westborough Recreation Department’s community playground. Let the kids enjoy the swings and slides while you relax on a bench or join in on the fun. Consider packing a light lunch to enjoy at the picnic area afterward.

evening
:

As evening approaches, return home for a family movie night complete with popcorn and cozy blankets. Choose a classic family film that everyone can enjoy, and let the laughter bring you closer together. Complete the day with a discussion about what everyone loved most about the day.

day 5
Art and Culture Extravaganza
morning
:

Dedicate your morning to exploring local art by visiting the nearby Worcester Art Museum. Spend time appreciating diverse art collections and engaging in any available workshops or family activities. This stimulating experience can ignite your creativity and set a vibrant tone for the day.

afternoon
:

In the afternoon, take a scenic drive to nearby cultural hotspots in Worcester for additional galleries and exhibitions. Enjoy lunch at a trendy café before venturing into local artistic endeavors. This exploration will broaden your perspective on regional art and its influence.

evening
:

As night falls, return to Westborough and attend a local theater performance or art showcase, immersing yourself in the vibrant arts community. This evening out allows you to support local artists while enjoying engaging performances. Conclude your cultural day with a relaxing dinner at a restaurant that features local artwork.

day 6
Sports and Recreation Day
morning
:

Start your day with a jog or bike ride along the scenic paths of the Westborough Country Club. The well-maintained trails offer beautiful views and other fitness enthusiasts to share the experience with. This active morning sets a motivated pace for the rest of the day.

afternoon
:

In the afternoon, gather some friends for a round of golf or tennis at the club, enjoying the friendly competition and beautiful weather. If you prefer something more relaxed, take a leisurely stroll through local parks or play Frisbee with family. This shared time in the outdoors enhances camaraderie and fun.

evening
:

As the day winds down, head to a local sports bar to enjoy dinner while watching any evening games on television. Relish in the lively atmosphere that comes with the enthusiasm of fellow sports fans. Conclude your day with laughter and spirited discussions about favorite teams.

day 7
Festivals and Markets
morning
:

On this day, awaken early to catch the bustling Westborough Farmers Market where you can explore fresh produce, artisanal goods, and local crafts. Chat with vendors to learn about their products and pick out delicious ingredients for your meals. This lively atmosphere will kick-start your day with fresh energy.

afternoon
:

Stick around at the market for live music and cooking demonstrations that highlight local culinary talents. Afterward, take part in any workshops offered by local artisans, creating your own crafts to take home. Spend some time enjoying the local flavors through sampling various dishes from food stalls.

evening
:

As evening sets in, be sure to attend a festival or community event where you can experience various cultural displays, music, and dancing. Join in on the fun, as this is a perfect opportunity to connect with locals and learn about their traditions. Cap off the day with a night stroll through market stalls filled with handmade gifts.

day 8
Wellness and Relaxation
morning
:

Begin your wellness day with a serene morning yoga session at a local studio or park to center your mind and body. The calming environment and gentle guidance from an instructor will help you reset and recharge. This mindful beginning paves the way for a day focused on relaxation.

afternoon
:

After yoga, indulge in a soothing spa treatment at a wellness center; choose from massages, facials, or aromatherapy sessions tailored just for you. Invite a friend to share the experience, enhancing both relaxation and connection. Spend the afternoon unwinding, allowing your stress to melt away.

evening
:

As the day wraps up, enjoy a wholesome dinner at a health-conscious restaurant that focuses on nutritious and delicious meals. Reflect on the rejuvenating experiences of the day and relish the calming atmosphere. As you wind down, spend some time journaling or meditating, wrapping up your wellness journey.

day 9
Community Engagement
morning
:

Use the morning hours to volunteer at a local shelter or community garden, lending your time to help others in need. Engaging with the community fosters connections and gives back in meaningful ways. This altruistic start fills your day with purpose and positivity.

afternoon
:

After volunteering, take time to enjoy lunch with fellow volunteers, discussing your experiences and building friendships in the process. Explore any nearby shops or parks that can help deepen your connection with the local area. Share stories and laughter over meals to continue the day’s good vibes.

evening
:

In the evening, attend a community meeting or town event to engage with local initiatives, hear from leaders, and share your ideas. This is a great opportunity to become more invested and inspired by the community's growth. As you return home, feel fulfilled from a day dedicated to making a difference.

Discover Westborough

Read more in our Westborough 2025 Travel Guide.

Westborough Travel Guide