New England Fall Color Tour: Vermont & New Hampshire

Sep 27 – Oct 3

Vermont & New Hampshire

Travel With Olivet


Register

September 27-October 3, 2026

Travel with Olivet

Experience autumn in New England, where history, charm and natural beauty come together in a tapestry of brilliant color. Begin in Boston, walking the Freedom Trail and exploring Boston Commons before journeying north to the White Mountains of New Hampshire. Stay at the grand Omni Mount Washington Resort, where elegant architecture meets sweeping mountain views. Travel scenic byways like the Kancamagus Highway, stop at cascading waterfalls and ride a vintage train through vibrant fall foliage. Continue into Vermont to visit the storybook village of Stowe and the beloved von Trapp Family Lodge, where Austrian heritage meets Green Mountain serenity. Sample fresh cider at Cold Hollow Cider Mill, enjoy a taste of whimsy at the Ben & Jerry’s Factory and witness craftsmanship at Simon Pearce Mill. Conclude your journey in Woodstock and return to Boston with memories of crisp mountain air, charming towns and the unforgettable beauty of New England in the fall.

This trip will sell-out quickly, so register online today. For questions, email Mr. Erinn Proehl at eproehl@olivet.edu or call 815-928-5553

Trip Highlights

  • Freedom Trail Walk – Follow the historic path that tells the story of America’s fight for independence.
  • Boston Commons – Stroll through the nation’s oldest public park in the heart of the city.
  • Faneuil Hall Marketplace & Quincy Market – Experience Boston’s historic center of commerce and conversation.
  • Omni Mount Washington Resort – Stay at a grand mountain retreat known for its panoramic views and timeless elegance.
  • Sunset from the Verandah at Omni Mount Washington Resort – Take in sweeping mountain views as the sun sets over the Presidential Range.
  • Kancamagus Highway – Ride on one of America’s most scenic byways through the heart of the White Mountains.
  • Scenic Fall Foliage Train Ride – Enjoy a nostalgic journey by rail through valleys filled with brilliant autumn color.
  • Diana’s Baths – Discover a peaceful series of cascading waterfalls surrounded by forest.
  • Silver Cascade – Stop for a photo at this striking roadside waterfall within Crawford Notch.
  • Franconia Notch State Park – Explore one of New Hampshire’s most iconic natural areas, home to rugged peaks and tranquil lakes.
  • Crawford Notch – Travel through a mountain pass filled with history and unmatched fall scenery.
  • von Trapp Family Lodge and Resort – Visit the mountain estate founded by the real von Trapp family of The Sound of Music.
  • Stowe, VT – Experience the charm of a classic New England village surrounded by the Green Mountains.
  • Cold Hollow Cider Mill – Sample fresh cider and apple treats at one of Vermont’s most beloved stops.
  • Ben & Jerry’s Factory Tour – Tour the factory and enjoy the iconic flavors that made Vermont famous.
  • Woodstock, VT – Explore one of Vermont’s prettiest small towns, complete with covered bridges and boutique shops.
  • Simon Pearce Mill – Watch skilled glassblowers at work in this scenic riverside workshop and gallery.
  • Covered Bridges – See traditional wooden bridges that capture the charm of rural New England.
  • Fall Foliage – Witness the brilliant color that draws travelers from around the world each autumn.

Cost & More Information

The total trip cost is $3,540, per person. Includes tour transportation, hotels, all meals, gratuities and more. Estimated flight cost is $387 per person.

Single occupancy supplement of $1,600.

Terms & Conditions

Trip Itinerary

Day 1 – Sunday, September 27: Arrival in Boston
Arrive in Boston and transfer to the Hyatt Regency Boston Harbor, conveniently located near the airport and waterfront. Gather for a welcome dinner where travelers can meet one another and review the week ahead.

Day 2 – Monday, September 28: Boston to the White Mountains
Begin the day with a walk along the Freedom Trail, visiting historic sites that trace the steps of the American Revolution. Enjoy time in Boston Commons before departing for Bretton Woods, New Hampshire. Upon arrival, check into the Omni Mount Washington Resort and enjoy dinner on the terrace with beautiful mountain views.

Day 3 – Tuesday, September 29: Explore the White Mountains
Spend the day traveling the scenic Kancamagus Highway, known for its outstanding fall foliage. Stop in North Conway for lunch, then visit Diana’s Baths and Silver Cascade to see two of the area’s most picturesque waterfalls. Conclude the day with dinner at Fabyan’s Station, a historic rail depot restaurant.

Day 4 – Wednesday, September 30: Travel from Bretton Woods to Stowe
Enjoy breakfast before taking a ride on the Bretton Woods Skyway Gondola, offering panoramic views of the mountains. Continue north to Vermont and check in at the von Trapp Family Lodge, where a guided history tour provides insight into the family’s legacy. Dinner is served in the main dining room overlooking the Green Mountains.

Day 5 – Thursday, October 1: Stowe and Vermont Highlights 
Start the morning with a visit to Cold Hollow Cider Mill for fresh cider and baked goods, then enjoy free time to explore historic downtown Stowe. In the afternoon, tour the Ben & Jerry’s Factory before returning to enjoy the lodge and dinner in the Mozart Room.

Day 6 – Friday, October 2: Woodstock and Return to Boston
Depart the lodge and travel to Woodstock, Vermont, known for its covered bridges and historic downtown. Visit the Simon Pearce Mill to observe artisans at work before returning to Boston. Conclude the trip with a farewell dinner featuring fresh regional cuisine and views of the harbor.

Day 7 – Saturday, October 3: Departure
After breakfast, transfer to the airport for return flights home, taking with you lasting memories of a classic New England fall experience.