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Massachusetts/New York

On the Road: Autumn in the Berkshires and Hudson Valley

Program No. 21402RJ
Treat your senses to an exploration of classic New England as you discover vibrant foliage, picturesque towns, the Norman Rockwell Museum and historic Red Lion Inn in Stockbridge.
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Regional StudiesHomes & GardensOn the Road
Length
8 days
Rating (4.95)
Activity Level
Starts at
3,299

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LODGING & MEALS
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Showing Lodging & Meals For:
Oct 18, 2025 - Oct 25, 2025 (Boston, MA to Connecticut)
Sep 06, 2025 - Sep 13, 2025 (Boston, MA to Connecticut)
Sep 13, 2025 - Sep 20, 2025 (Boston, MA to Connecticut)
Oct 11, 2025 - Oct 18, 2025 (Boston, MA to Connecticut)
Oct 18, 2025 - Oct 25, 2025 (Boston, MA to Connecticut)
Sep 19, 2026 - Sep 26, 2026 (Boston, MA to Connecticut)
Sep 26, 2026 - Oct 03, 2026 (Boston, MA to Connecticut)
Oct 03, 2026 - Oct 10, 2026 (Boston, MA to Connecticut)
Oct 17, 2026 - Oct 24, 2026 (Boston, MA to Connecticut)
Oct 24, 2026 - Oct 31, 2026 (Boston, MA to Connecticut)
Lodging and meal options may differ by date. Select a date to see the information specific to that date.
What You'll Eat
7 Breakfasts
4 Lunches
5 Dinners
Total: 16 Meals
The following choices may be available when requested in advance: Vegetarian, Low Salt, Low Fat, Gluten Free
Where You'll Stay
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews
Hilton Boston Logan Airport
Visit Site
1 NIGHT
Location: Boston
The Hilton Boston Logan Hotel is located right next to the Logan Airport. Many of the rooms offer an airport view or a Boston city view. The hotel connects to terminals A and E and has 24-hour shuttle access. With so many restaurants and attractions just a short walk from the hotel, you're sure to find something perfect for you.
TripAdvisor Reviews
Red Lion Inn
Visit Site
3 NIGHTS
Location: Stockbridge
The Red Lion is one of the most famous of New England’s historic inns, situated in the heart of charming Stockbridge village. Featuring state-of-the-industry amenities amid fine antiques and art, The Red Lion Inn offers outstanding cuisine by a James Beard House-featured chef who supports local farms, an award-winning wine list and four distinct dining experiences. The Red Lion is central to the Berkshires’ many arts attractions and outdoor recreation, and is just a few minutes from the Norman Rockwell Museum and Tanglewood. Each room at the Inn exudes it's own distinctive style and character. No two rooms are the same and have unique features.
TripAdvisor Reviews
Holiday Inn Express Poughkeepsie
Visit Site
2 NIGHTS
Location: Poughkeepsie
TripAdvisor Reviews
Hampton Inn of Danbury
Visit Site
1 NIGHT
Location: Danbury
Minutes from I-84 with great links to Stamford and New York, this Danbury, Connecticut hotel offers small-town charm with contemporary conveniences. Browse a diverse mix of stores in downtown Danbury or swim, boat and fish the clear waters of Candlewood Lake.
TripAdvisor Reviews





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