Dedham

Day Trips

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

day 1
Exploring Historic Center
morning
:

Start your day by visiting the Dedham Historical Society and Museum, where you can learn about the rich history of the area. Afterward, stroll through the charming streets of Dedham Square, admiring the historic architecture and local shops. Enjoy a fresh cup of coffee at a local café as you take in the sights and sounds of this quaint town.

afternoon
:

Head to the nearby Dedham Community Theatre, a charming venue that often shows classic films and indie flicks. Grab lunch at a popular local eatery, savoring some New England clam chowder or a lobster roll. After your meal, take a leisurely walk through the nearby Endicott Estate, enjoying its beautiful gardens and serene surroundings.

evening
:

As the sun sets, return to Dedham Square for dinner at one of the many restaurants offering a variety of cuisines. Consider indulging in some local seafood or a hearty steak at a cozy steakhouse. End your evening with a stroll through the square, perhaps catching a live music performance or simply enjoying the peaceful atmosphere.

day 2
Nature Trails and Parks
morning
:

Begin your day with a visit to the beautiful Wilson Mountain Reservation, where you can hike the scenic trails that offer stunning views of the surrounding landscape. The fresh morning air and the sounds of nature will invigorate you as you explore the various paths. Bring along a packed breakfast to enjoy at one of the scenic overlooks.

afternoon
:

After your hike, head to the nearby Dedham Park for a relaxing afternoon picnic. Enjoy your packed lunch under the shade of the trees, and take advantage of the park's amenities like walking paths and playgrounds. If you're feeling adventurous, rent a bike and explore the bike trails that wind through the park.

evening
:

As the day winds down, visit a local brewery for a tasting of craft beers brewed right in Dedham. Pair your drinks with some light appetizers while mingling with locals and enjoying the laid-back atmosphere. If the weather permits, sit outside and soak in the evening ambiance.

day 3
Cultural Exploration at Museums
morning
:

Spend your morning at the Museum of Bad Art, a unique and quirky destination that showcases art that is intentionally 'bad.' This lighthearted museum will surely bring a smile to your face as you explore its unusual exhibits. Afterward, visit the nearby Dedham Art Association, where you can peruse local artwork and perhaps even chat with some of the artists.

afternoon
:

Take a break for lunch at a nearby café, savoring homemade sandwiches and pastries. Post-lunch, immerse yourself in the history of the area with a visit to the Fairbanks House, the oldest surviving wooden house in North America. The guided tour will give you insights into colonial life and the architectural features of the house.

evening
:

In the evening, treat yourself to a fine dining experience at one of Dedham's upscale restaurants. Enjoy a multi-course meal featuring seasonal ingredients and local flavors. After dinner, consider attending a live performance at the Dedham Community Theatre or enjoying a quiet evening stroll through the town.

day 4
Shopping and Culinary Delights
morning
:

Kick off your day with a visit to the Dedham Farmers Market, where you can browse fresh produce, artisanal goods, and locally made products. Engage with the friendly vendors and perhaps pick up ingredients for a picnic later in the day. Enjoy a light breakfast at one of the food stalls, sampling homemade pastries or breakfast burritos.

afternoon
:

After shopping, head to the historic Dedham Square to explore its unique boutiques and specialty shops. Don’t miss the opportunity to taste local chocolate or artisanal cheeses as you shop. Afterward, have lunch at an inviting bistro known for its farm-to-table philosophy.

evening
:

As the sun sets, participate in a cooking class at one of Dedham’s culinary schools, where you'll learn to prepare a delicious local dish. Enjoy the fruits of your labor as you dine on your creation, paired with wine. Cap off the night with dessert at a local ice cream shop, indulging in unique flavors that reflect the region.

day 5
Outdoor Adventure at the Charles River
morning
:

Start your day with a canoe or kayak rental at the Charles River, where you can paddle along the scenic waters while enjoying the natural beauty of the area. The calm morning is perfect for spotting local wildlife and embracing the tranquility of the river. Pack a light snack to enjoy while you’re out on the water.

afternoon
:

After your water adventure, relax with a leisurely lunch at a riverside café, enjoying views of the water. Once you've refueled, take a scenic walk along the Charles River Reservation, soaking in the fresh air and picturesque landscapes. Look for spots to take photographs, capturing the beauty around you.

evening
:

In the evening, find a cozy spot along the riverbank to watch the sunset, with the golden hour reflecting off the water. Consider bringing a portable grill for a relaxed barbecue dinner as the day winds down. Enjoy the peaceful sounds of nature and perhaps a few stargazing moments as night falls.

day 6
Day of Relaxation and Wellness
morning
:

Start your day with a rejuvenating yoga class at a local studio, surrounded by the calming ambiance of Dedham. The instructor will guide you through a series of poses that will help you stretch, breathe, and ease into the day. After class, enjoy a healthy breakfast smoothie at a nearby café to fuel your body for the day ahead.

afternoon
:

Treat yourself to a spa afternoon, where you can indulge in a massage or facial that will leave you feeling refreshed and pampered. Enjoy the serene atmosphere and take advantage of the spa's relaxation areas. Afterward, savor a light lunch at a health-focused eatery, featuring fresh salads and grain bowls.

evening
:

As the day comes to an end, participate in a guided meditation session at a local wellness center, allowing you to reflect on the day and find inner peace. Follow this with a nourishing dinner at a restaurant known for its organic and locally sourced dishes. Wind down your evening with a warm cup of herbal tea, embracing the calmness of the night.

day 7
Family Fun Day
morning
:

Start your family adventure with a visit to the Dedham Community Pool, where the kids can splash around while you relax on the sidelines. Enjoy the sunny morning by playing games or just lounging by the pool. Bring along some snacks to keep everyone energized for the day ahead.

afternoon
:

After some fun in the sun, head to a local park with playgrounds and picnic areas for a family lunch. Enjoy sandwiches and fresh fruit while the kids play on the swings and slides. After lunch, consider visiting a nearby bowling alley for some friendly family competition.

evening
:

Cap off your family day with a visit to a local ice cream shop where everyone can choose their favorite flavors. Share stories from the day while enjoying your sweet treats. Finish the night with a family movie night at home, complete with popcorn and cozy blankets.

day 8
Dine Around Dedham
morning
:

Begin your culinary journey with breakfast at a beloved local diner, where you can enjoy classic American breakfast staples like pancakes and omelets. Engage with friendly staff and locals as you savor your meal in a cozy atmosphere. After breakfast, take a short walk to a nearby bakery for some fresh pastries to take along.

afternoon
:

For lunch, explore Dedham’s diverse dining scene by visiting a food truck or casual eatery that offers international cuisine. Sample dishes from different cultures, making for a fun and exciting lunch experience. Afterward, visit a local chocolatier for a sweet treat or a behind-the-scenes look at how chocolates are made.

evening
:

In the evening, enjoy dinner at an upscale restaurant that offers a tasting menu, allowing you to experience multiple courses crafted with seasonal ingredients. Pair your meal with a selection of wines from local vineyards for a truly memorable dining experience. Conclude your culinary adventure with a nightcap at a nearby bar, where you can reflect on the day’s delicious discoveries.

Discover Dedham

Read more in our Dedham 2025 Travel Guide.

Dedham Travel Guide