5-Day New England Fall Foliage Road Trip in Massachusetts

Day 1: Explore Boston

Boston, USA

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your day with a delicious breakfast of freshly baked pastries and artisanal coffee at Tatte Bakery & Cafe.
Located in Brookline, just a short drive from Boston.
USD 20, 1 hour

9:30AM

Boston Public Garden

Stroll through the stunning Boston Public Garden to witness early fall colors, with swan boats gliding across the lagoon.
Easily walkable from Tatte Bakery.
Free, 1.5 hours

11:00AM

Freedom Trail

Traverse the historic Freedom Trail, marking significant sites and monuments in Massachusetts history.
Begin at Boston Common and follow the red-brick path.
Free, 2 hours

1:00PM

Lunch at The Barking Crab

Enjoy a quintessential New England seafood lunch at The Barking Crab, known for its casual outdoor seating and fresh seafood.
Located along the waterfront, accessible by car or rideshare.
USD 50, 1.5 hours

2:30PM

Visit the Museum of Fine Arts

Explore the impressive collections at the Museum of Fine Arts, home to beautiful American art including stunning autumn landscapes.
Drive and park at the museum.
USD 25, 2 hours

4:30PM

Harvard Yard

Wander around historic Harvard Yard in Cambridge, where you'll appreciate the ivy-covered brick buildings, vibrant fall foliage, and student life.
Drive over to Cambridge; parking available nearby.
Free, 1 hour

6:00PM

Dinner at Legal Sea Foods

Savor a delightful dinner of clam chowder and fresh catch at Legal Sea Foods, a Massachusetts favorite.
Head back towards Boston to enjoy your dinner.
USD 70, 1.5 hours
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Day 2: North Shore Adventure

Ipswich & Rockport, USA

8:00AM

Breakfast at The Coffee Shop

Fuel up with classic American breakfast options at The Coffee Shop, a cozy spot in Boston before heading out.
Short drive from your hotel in Boston.
USD 25, 1 hour

9:30AM

Visit Crane Beach

Enjoy a picturesque morning walk on Crane Beach, blanketed in vibrant fall colors and tranquil views of the Atlantic.
A scenic drive to Ipswich should take about 45 minutes.
USD 35, 1.5 hours

11:30AM

Explore Ipswich Historic District

Wander the historic charm of Ipswich, admiring well-preserved homes set amidst fall foliage.
Short drive into the district.
Free, 1.5 hours

1:00PM

Lunch at The Clam Box

Indulge in crispy fried clams at The Clam Box, a local seafood shack that's a must-visit.
Just a short drive from the Historic District.
USD 30, 1 hour

2:30PM

Scenic Drive to Rockport

Take a scenic drive along Route 127 to Rockport, admiring coastal views and lovely landscapes along the way.
Around 30 minutes to Rockport.
Free, 1 hour

3:30PM

Explore Rockport's Bearskin Neck

Wander through the quaint shops and galleries of Bearskin Neck, enjoying the unique coastal atmosphere.
Easily walkable once you park in town.
Free, 2 hours

6:00PM

Dinner at The Lobster Pot

Delight in a delicious dinner of lobster and seafood specialties at The Lobster Pot, offering great views of the harbor.
Located right in Rockport.
USD 60, 1.5 hours
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Day 3: Berkshires Bliss

Lenox & Stockbridge, USA

8:00AM

Breakfast at Haven Cafe & Bakery

Savor a hearty breakfast at Haven Café, known for its farm-fresh ingredients and delicious baked goods.
Head back towards Boston, then drive west to the Berkshires.
USD 25, 1.5 hours

9:30AM

Visit The Mount

Explore Edith Wharton's stunning estate, enjoying the beautiful gardens filled with vibrant autumn colors.
Located in Lenox, about 25 minutes from your breakfast spot.
USD 20, 2 hours

11:30AM

Berkshire Botanical Garden

Stroll through the Berkshire Botanical Garden, where the fall blossoms create a beautiful backdrop.
Short drive from The Mount.
USD 10, 1.5 hours

1:00PM

Lunch at The Red Lion Inn

Enjoy a classic New England lunch at The Red Lion Inn with locally-sourced ingredients.
In Stockbridge, a quick drive from the Botanical Garden.
USD 50, 1.5 hours

2:30PM

Visit Norman Rockwell Museum

Delve into the world of beloved illustrator Norman Rockwell at his eponymous museum.
Just a quick drive from your lunch spot.
USD 20, 2 hours

4:30PM

Scenic drive through Mt. Greylock

Take a scenic drive through Mt. Greylock State Reservation to catch breathtaking views of the fall foliage.
Head northwest for about 30 minutes.
Free, 1.5 hours

6:00PM

Dinner at Salvatore's

Wrap up your day with delicious Italian entrees at Salvatore's, featuring locally-sourced ingredients.
Return towards Lenox area for dinner.
USD 50, 1.5 hours
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Day 4: Pioneer Valley Exploration

Amherst & Northampton, USA

8:00AM

Breakfast at The Breakfast Ramen

Kick off your morning with a unique ramen breakfast at The Breakfast Ramen in Northampton.
Driving roughly 1 hour from Lenox.
USD 25, 1 hour

9:30AM

Visit Mount Tom State Reservation

Hike the trails at Mount Tom State Reservation for stunning panoramic views of the colorful fall foliage.
Just a quick 20-minute drive from breakfast.
Free, 2 hours

11:30AM

Explore Historic Northampton

Discover the local cultural heritage at Historic Northampton with its beautiful gardens and museums.
Quick drive back to Northampton center.
Free, 1.5 hours

1:00PM

Lunch at Tryon’s

Enjoy contemporary American lunch at Tryon’s with a seasonal menu featuring local produce.
Located in downtown Northampton.
USD 40, 1.5 hours

2:30PM

Visit Smith College Botanic Garden

Wander through the tranquil grounds of the Smith College Botanic Garden, perfect for observing fall colors.
Just a short walk from Tryon’s.
Free, 1.5 hours

4:00PM

Drive to Hadley

Head towards Hadley to explore local farms and scenery filled with autumnal hues.
About a 15-minute drive.
Free, 1 hour

5:00PM

Dinner at The Alvah Stone

Finish your day at The Alvah Stone, a cozy restaurant known for its farm-to-table dishes.
Drive about 30 minutes back toward Northampton.
USD 55, 1.5 hours
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Day 5: Return to Boston

Boston, USA

8:00AM

Breakfast at Blackbird Doughnuts

Start your final day in Boston with gourmet doughnuts at Blackbird Doughnuts, known for innovative flavors.
Short drive from your hotel.
USD 20, 1 hour

9:30AM

Visit Boston Harbor

Take a leisurely stroll along the Boston Harborwalk and enjoy the views of the vibrant fall scenery by the water.
Drive and park near the waterfront.
Free, 1.5 hours

11:00AM

Explore the Boston Tea Party Ships & Museum

Engage in the interactive exhibits at the Boston Tea Party Ships & Museum and learn about American history.
Adjacent to the harbor, an easy walk from the harbor.
USD 30, 1.5 hours

1:00PM

Lunch at The Capital Grille

Indulge in a sumptuous lunch at The Capital Grille, renowned for its fine steak and wine selection.
Short drive from the museum.
USD 70, 1.5 hours

2:30PM

Visit the Isabella Stewart Gardner Museum

Conclude your trip with a visit to Isabella Stewart Gardner Museum, famed for its stunning architecture and art collection.
Drive to the museum, parking available on-site.
USD 15, 2 hours

5:00PM

Departure

Reflect on your incredible fall journey through Massachusetts as you prepare for your departure.
Head to Boston Logan Airport for your flight.
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