5-Day Fall Foliage Tour of Massachusetts

Day 1: Explore Boston

Boston, MA on October 5, 2024

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your day with a delicious breakfast of fresh pastries and a coffee at this charming local cafe.
Located near the Charles River, it’s a great kickoff point for your Boston adventure.
USD25, 1 hour

9:30AM

Visit Boston Common & Public Garden

Stroll through the historic Boston Common and the beautifully landscaped Public Garden, where fall colors are beginning to emerge.
A short walk of about 15 minutes from Tatte.
USD0, 1.5 hours

11:00AM

Freedom Trail Walk

Begin your walk along the Freedom Trail, exploring the historic sites while enjoying the vibrant fall backdrop.
The trail starts at Boston Common, making it an easy next step.
USD0, 2 hours

1:00PM

Lunch at Quincy Market

Grab lunch at Quincy Market, exploring a variety of food stalls that offer local specialties and seasonal fare.
It's nestled between the historic buildings and is easily accessible after your walk.
USD20, 1 hour

2:30PM

New England Aquarium

Dive into the wonders of the ocean at the New England Aquarium where the exhibits are both fun and educational.
Located just a 10-minute walk from Quincy Market.
USD30, 2 hours

4:30PM

Head to North End for Dinner

Enjoy an authentic Italian dinner at Mamma Maria, known for its homemade pasta and warm service.
A 15-minute walk to the North End.
USD80, 1.5 hours

6:30PM

Evening Stroll Along the Waterfront

Finish your day with a peaceful walk along Boston's waterfront, admiring the skyline as the sun sets.
A short walk from Mamma Maria.
USD0, 1 hour
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Day 2: North Shore Adventures

Rockport, MA on October 6, 2024

7:00AM

Breakfast at The Coffee Shop

Fuel up with fresh, locally roasted coffee and hearty breakfast sandwiches before hitting the road.
A quick drive from your hotel, just about 10 minutes.
USD25, 1 hour

8:30AM

Drive to Cape Ann

Head to Cape Ann to admire the stunning coastline and fall foliage as you drive along scenic Route 127.
It’s approximately a 45-minute drive to Cape Ann.
USD0, 1 hour

9:30AM

Explore Rockport & Bearskin Neck

Enjoy exploring the picturesque streets of Rockport, filled with colorful fall scenery and quaint shops.
You can park easily in town and start your exploration.
USD0, 2 hours

11:30AM

Lunch at the Lobster Pool

Indulge in fresh seafood while taking in views of the ocean, a perfect spot for fall photos.
A short drive from Rockport, about 10 minutes.
USD35, 1 hour

1:00PM

Visit Halibut Point State Park

Hike the trails of Halibut Point for breathtaking views of the quarry and coastline, surrounded by vibrant autumn colors.
It's a 15-minute drive from The Lobster Pool.
USD0, 2 hours

3:30PM

Drive to Ipswich

Head inland to explore the charming town of Ipswich, famous for its historic homes and natural greenery.
It's a 30-minute drive from Halibut Point.
USD0, 30 minutes

4:00PM

Explore the Ipswich River Wildlife Sanctuary

Wander the scenic trails at the sanctuary, experiencing the rich diversity of wildlife against the backdrop of colorful foliage.
Easily accessible from the town center.
USD7, 1.5 hours

5:30PM

Dinner at The Clam Box

Savor the famous fried clams at The Clam Box, a local favorite with a nostalgic vibe.
Just a short drive from the sanctuary back into Ipswich.
USD40, 1 hour

7:00PM

Return to Boston Hotel

Drive back to Boston, reflecting on the beautiful day while enjoying the evening views.
It's roughly a 40-minute drive back.
USD0, 40 minutes
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Day 3: Central Massachusetts

Sturbridge, MA on October 7, 2024

7:30AM

Breakfast at Morgan’s

Start your day with a farm-to-table breakfast featuring local ingredients at this popular spot in Boston.
Easily accessible and about 10 minutes from downtown.
USD30, 1 hour

9:00AM

Drive to Old Sturbridge Village

Travel to this living history museum that showcases early 19th-century rural life, surrounded by beautiful fall foliage.
A straightforward route of about 1 hour long.
USD28, 1 hour

10:00AM

Explore Old Sturbridge Village

Engage with costumed historians and participate in hands-on activities as you wander through the recreated village.
Plan to spend several hours here for a rich experience.
USD28, 3 hours

1:00PM

Lunch at the Village Restaurant

Enjoy a hearty lunch featuring locally sourced ingredients right on the museum's grounds.
Conveniently located within Old Sturbridge Village.
USD20, 1 hour

2:30PM

Discover Wells State Park

Take a scenic drive to Wells State Park and enjoy a leisurely hike amid colorful trees.
A quick 20-minute drive from Sturbridge.
USD0, 2 hours

4:30PM

Browse Local Shops in Sturbridge

Explore charming local shops and boutiques for autumn-inspired gifts and souvenirs.
Return back to Sturbridge center which is about a 20-minute drive.
USD0, 1 hour

6:00PM

Dinner at The Publick House

Indulge in a classic New England meal at this historic tavern with a cozy atmosphere.
Located right in the heart of Sturbridge.
USD50, 1.5 hours

7:30PM

Return to Boston

Drive back to Boston and unwind after a day filled with history and nature.
About an hour's drive back.
USD0, 1 hour
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Day 4: Berkshire Exploration

Lenox, MA on October 8, 2024

7:30AM

Breakfast at Blueberry Hill

Delight in a fresh breakfast with homemade blueberry pancakes to kickstart your Berkshire adventure.
About a 10-minute drive from your hotel.
USD25, 1 hour

9:00AM

Drive to the Berkshires

Hit the road and soak in the fall foliage as you merge onto the scenic Route 7 towards Lenox.
It's a beautiful drive of about an hour.
USD0, 1 hour

10:00AM

Visit the Norman Rockwell Museum

Explore the art of Norman Rockwell and the beautiful grounds that are impeccably decorated with fall plants.
The museum is centrally located in Stockbridge.
USD20, 1.5 hours

11:30AM

Fall Foliage Drive through the Berkshires

Take a leisurely drive through the Berkshires, stopping at scenic viewpoints to capture the breathtaking landscapes.
You can pick various routes, Route 7 and 20 are ideal.
USD0, 2 hours

1:30PM

Lunch at The Red Lion Inn

Savor a delicious meal at this historic inn, known for its comforting New England classics.
Conveniently located in Stockbridge.
USD35, 1.5 hours

3:00PM

Hike at Mt. Greylock State Reservation

Embark on a scenic hike with panoramic views at the highest point in Massachusetts amidst vibrant fall foliage.
A short 30-minute drive from Stockbridge.
USD0, 3 hours

6:30PM

Dinner at The Gateway Grill

End your day with a cozy dinner at The Gateway Grill, enjoying a farm-to-table experience.
A short drive from the state reservation back to Lenox.
USD50, 1.5 hours

8:00PM

Return to Boston

Drive back to Boston, filled with memories and picturesque views of the vibrant fall colors.
The return trip to Boston takes about 2 hours.
USD0, 2 hours
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Day 5: Relax in Boston

Boston, MA on October 9, 2024

8:00AM

Breakfast at Flour Bakery

Treat yourself to a scrumptious breakfast pastry and coffee at this beloved Boston eatery.
Located about 10 minutes from downtown.
USD20, 1 hour

9:30AM

Walk along the Charles River Esplanade

Enjoy a peaceful morning walk along the Esplanade, surrounded by stunning views and potential remnants of fall colors.
Easily accessed from Flour Bakery.
USD0, 1 hour

10:30AM

Visit the Isabella Stewart Gardner Museum

Explore the unique and beautiful museum, where the gardens may still be showcasing the exquisite colors of fall.
Less than a 10-minute drive or 15-minute walk.
USD20, 1.5 hours

12:00PM

Lunch at The Capital Grille

Dine at The Capital Grille where a refined atmosphere accompanies a menu rich in seasonal dishes.
A 10-minute drive from the museum.
USD40, 1.5 hours

1:30PM

Shopping in Back Bay

Indulge in shopping at the upscale boutiques and historic streets of Back Bay, wrapping up your trip with a slice of local culture.
Only a short drive or walk from The Capital Grille.
USD0, 3 hours

4:30PM

Return the Rental Car

Necessary before your departure; ensure everything is settled before saying goodbye to Boston.
Head to the nearest rental location, approximately a 15-minute drive.
USD0, 1 hour
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