New England Fall Foliage & Pumpkin Regatta!

October 8 – 14, 2025

7 Days & 6 Nights

Tour ID: T462

$4,299.00 Per person, double occupancy
$5,499.00 Per person, single occupancy

Sightseeing Highlights

• Boston
• Montpelier, VT
  • Ben & Jerry’s Factory
  • Cold Hollow Cider Mill
  • Morse Farm Maple Sugarworks
  • Bar Hill Distillery
• White Mountain National Forest
• Kancamagus Highway
• Mount Washington Cog Railway
• Portland Maine
  • Portland Headlight lighthouse in Cape Elizabeth
• Damariscotta Pumpkin Regatta
• Freeport
• Kennebunkport

Tour Price Includes:

• Roundtrip Airfare
• Round Trip Airport
• Transportation
• Deluxe Motorcoach
• Professional Tour
• Director
• Luggage Handling
• Meals:
  • 6 Breakfasts
  • 2 Lunches
  • 2 Dinners
• Boston, MA (2 nights)
• Montpelier, VT (1 Night)
• North Conway, VT (1 Night)
• Portland, ME (2 Nights)

Itinerary

Day 1 (Oct 8) – Arrival in Boston: Kick off your adventure by flying into the historic city of Boston. Immerse yourself in the vibrant atmosphere as you prepare for an unforgettable journey through New England, where the fall foliage will greet you with a stunning array of
colors. (1 Night Boston Area)
Day 2 (Oct 9) – Montpelier, VT and Surroundings: Today, we travel to Montpelier, the capital of Vermont. Visit the quirky Ben & Jerry’s factory and Flavor Graveyard. Explore Morse Farm Maple
Sugarworks for a sweet taste of local tradition, all amidst the beautiful backdrop of fall foliage. Later visit the Bar Hill Distillery and enjoy their unique spirits. (Overnight Montpelier VT) B

Day 3 (Oct 10) -Scenic Drives and Mountain Views:  Enjoy self-guided tour at Cold Hollow Cider Mill, where you can savor a delicious apple cider donut and a refreshing sip of apple cider.  Embark on a picturesque drive along the 34-mile Kancamagus Highway, surrounded by the stunning White Mountain National Forest. Experience the thrill of boarding the Mount Washington Cog Railway to reach the summit of Mount Washington, the highest peak in New England. Enjoy a packed lunch as you take in the breathtaking views. (1 Night North Conway, NH) B, L

Day 4 (Oct 11) – Coastal Portland, ME: Depart the White Mountains for the coastal charm of Portland, Maine. Visit the historic Portland Headlight lighthouse in Cape Elizabeth. Enjoy free time in Portland to explore the city and have lunch on your own. (2 Nights Portland, ME.) B,D

Day 5 (Oct 12) – Pumpkin Festival: Experience the unique and entertaining Damariscotta Pumpkin Regatta. Hilarity ensues while people struggle to race on the water in hollowed out
giant pumpkins. Spend time exploring Damariscotta where streets are lined with elaborate giant decorated pumpkins. B, L

Day 6 (Oct 13) – Back to Boston: Today we make our way back to Boston. Stopping in the beautiful town of Freeport, known for the headquarters of LL Bean. Next, we will visit the quaint town of Kennebunkport, known for its beaches, lighthouses, and fresh seafood. Spend your final night in Boston, reflecting on the incredible journey. (1 Night Boston Area) B

Day 7 (Oct 14) – Departure: Conclude your New England adventure with a flight home, taking with you unforgettable memories and a longing to return. B

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