Wellesley

Day Trips

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

day 1
Arrival and Exploring the Campus
morning
:

Arrive in Wellesley and check into your accommodation. Start your day with a leisurely walk around the picturesque Wellesley College, admiring the beautiful architecture and tranquil nature trails. Take some time to visit the Wellesley College Botanic Gardens to soak in the lush greenery.

afternoon
:

After lunch, head to the Wellesley Farmers' Market, where you can savor local produce and homemade treats. Stroll through the surrounding artisan shops in Wellesley Square, discovering unique crafts and gifts. Treat yourself to coffee at a charming café while enjoying the local atmosphere.

evening
:

As the sun sets, dine at a local restaurant offering delicious seasonal dishes. Join a scheduled event or performance at the Wellesley College or nearby venues. Conclude the evening with a peaceful walk through the college campus under the starry sky.

day 2
Day Trip to Boston
morning
:

Catch the morning train to Boston and grab breakfast at a renowned café in the city. Spend the morning exploring the historic Freedom Trail, visiting sites such as Boston Common and Paul Revere’s House. Immerse yourself in the local culture as you soak in the vibrant atmosphere of the city.

afternoon
:

Have lunch at Quincy Market, sampling diverse culinary delights and local specialties. Continue your exploration by visiting the Boston Museum of Fine Arts, where you can admire an impressive collection of art. Don’t forget to stroll through Boston’s beautiful parks and public squares.

evening
:

Head back to Wellesley in the evening and enjoy dinner at a cozy restaurant. Unwind by attending a local theater performance or concert, allowing yourself to absorb the artistic culture of the area. Wrap up your day with a relaxing evening walk, reflecting on your Boston adventures.

day 3
Visit to the Massachusetts Audubon Society
morning
:

Begin your day with a visit to the Massachusetts Audubon Society's Broadmoor Wildlife Sanctuary. Enjoy the serenity of nature as you explore the diverse trails and habitats, perfect for birdwatching and wildlife spotting. Capture stunning views of the surrounding landscapes and take time to meditate amidst nature.

afternoon
:

Have a nature-inspired lunch at the sanctuary followed by a guided wildlife program, where you can learn about local ecosystems. Participate in hands-on activities that engage you with environmental conservation. Relax by the marshes, taking in the sounds of birds and the calming scenery.

evening
:

Return to Wellesley for a casual dinner with friends or family in a friendly eatery. Share stories about your wildlife adventures while enjoying your meal. As the night settles, consider stargazing in a nearby park, reminiscing about the day's experiences.

day 4
Cultural Day at Local Museums
morning
:

Start your day at the Wellesley College Davis Museum, home to an extensive collection of modern and historical art. Engage with various exhibitions and attend guided tours available to enhance your understanding. Allow yourself to be inspired by the creativity displayed throughout the galleries.

afternoon
:

After a delicious lunch at a local café, head to the nearby Armenian Library and Museum of America for a unique cultural experience. Explore the rich heritage of the Armenian community in America through photographs, artifacts, and historical exhibits. Spend time browsing their library resources dedicated to Armenian history and culture.

evening
:

Enjoy a scenic dinner at your favorite spot in Wellesley, sharing insights gained from the day's museum visits. Move on to a local bookshop or arts venue for an evening of poetry readings or art talks. Engage with the local artistic community and reflect on your cultural journey.

day 5
Outdoor Adventures in Local Parks
morning
:

Kick off your day with a hike at the beautiful Elm Bank Reservation, renowned for its scenic landscapes and flower gardens. Breathe in the fresh air as you explore various trails suitable for all skill levels. Capture the breathtaking views with your camera as you soak in the tranquility of your surroundings.

afternoon
:

Picnic in one of the designated areas at Elm Bank, enjoying some homemade treats or takeout from a nearby deli. After lunch, continue your outdoor adventure, perhaps renting bikes or canoes to explore the area in a different way. Embrace the outdoor lifestyle Wellesley has to offer.

evening
:

Return to Wellesley for an early dinner at a farm-to-table restaurant, celebrating the freshness of local produce. After dinner, participate in a community bonfire night if available, connecting with locals and sharing stories. End your night with a peaceful stroll through your favorite park.

day 6
Shopping and Dining in Wellesley Square
morning
:

Begin your day with a hearty breakfast at a local favorite, then head out for a shopping spree in Wellesley Square. Explore chic boutiques, specialty shops, and art galleries, searching for that perfect souvenir. Don't forget to take a coffee break at one of the quaint cafes along the way.

afternoon
:

Continue your shopping experience by visiting the local artisan shops, where you can find handmade goods and unique gifts. Enjoy lunch at a popular eatery known for its vibrant atmosphere and delicious menu. Spend your afternoon enjoying live music or a local art show if available.

evening
:

Celebrate your day of shopping with a fine dining experience at one of Wellesley’s upscale restaurants. Immerse yourself in the culinary delights of the local area, indulging in a multi-course meal. After dinner, consider attending a local event or wine tasting to wind down your evening.

day 7
Exploring Nature at Lake Waban
morning
:

Head to Lake Waban for a tranquil morning of leisure by the water’s edge. Start your day with a peaceful walk around the lake, appreciating the stunning views and natural beauty it offers. Bring along your journal to jot down your thoughts as you connect with nature.

afternoon
:

Pack a picnic lunch to enjoy by the lake, taking in the serene environment. After lunch, rent a kayak or paddleboard to explore the water, soaking in the surrounding scenery from a different perspective. Capture the moments that make your day special.

evening
:

Return to shore for a delightful dinner at a lakeside restaurant, relishing the enchanting views as the sun sets. Reflect on your day while enjoying a dessert with friends or family. End the evening with a relaxing stroll along the water, under the glow of the setting sun.

day 8
Historical Tour of Wellesley
morning
:

Embark on a historical walking tour of Wellesley, learning about its rich past and notable landmarks. Visit the Wellesley Historical Society to gather interesting facts and stories that shaped the town. Enjoy discovering historical homes and buildings dotted throughout the area.

afternoon
:

After a light lunch, spend your afternoon at the Wellesley College Archives and Special Collections, where you can uncover more about the college's history and its influential alumni. Participate in discussions or guided tours if available. Engage with exhibit topics that showcase the heritage of Wellesley.

evening
:

Wrap up your historical journey with dinner at a restaurant that highlights local ingredients and classic dishes. Share your historical insights with your dining companions, enriching your experience. Spend the late evening reflecting on Wellesley’s vibrant history and its role in the larger narrative of American education.

day 9
Relax and Reflect
morning
:

Dedicate this day to self-care by starting your morning with a calming yoga or meditation session at a local studio. Enjoy a light, nourishing breakfast that energizes you for the day ahead. Spend the morning journaling your experiences from the trip and setting intentions for the future.

afternoon
:

Treat yourself to a spa day in Wellesley, enjoying massages or rejuvenating treatments that soothe your body and mind. Indulge in quality time with a book or engage in contemplative walks in local botanical gardens. Use this time to appreciate the tranquility of your surroundings.

evening
:

Conclude your journey with a special dinner at a restaurant that offers a cozy atmosphere perfect for reflecting on your trip. Share a toast to the experiences you’ve collected and the memories you’ve created. Depart Wellesley feeling rejuvenated and inspired.

Discover Wellesley

Read more in our Wellesley 2025 Travel Guide.

Wellesley Travel Guide