New England Pre-trip Extension
New England (4 Days/3 Nights) | October 2026
Experience the charm of New England in peak autumn as we travel from Boston through Vermont’s rolling Green Mountains, New Hampshire’s dramatic White Mountains, and Maine’s iconic coastline. This beautifully curated journey blends scenic drives, charming towns, gentle nature walks, and classic regional experiences—from mountain valleys lined with fall color to historic seaside villages and heritage railway views. With cozy stays in Stowe and Portland, we will enjoy a perfect mix of outdoor beauty, small-town character, and coastal New England culture. This itinerary offers an inviting snapshot of the region’s landscapes and seasonal magic, making our four-day adventure both refreshing and unforgettable.
New England Itinerary
Day 1: October 4, 2026
Vermont's Green Mountain
Our journey begins with a morning departure from Boston, traveling northwest into the rolling landscapes of Vermont’s Green Mountains. As you cross into Vermont, the scenery shifts to pastoral countryside,
forested hills, and classic white-steepled villages.
Upon arrival in northern Vermont, we’ll explore the charming alpine town of Stowe or the craft-driven village of Waterbury, both known for their welcoming atmosphere, artisan shops, excellent coffee houses and bakeries.
Depending on weather and timing, optional short walks may include Moss Glen Falls, a picturesque cascade accessible via a short forest path, or scenic pull-offs along the winding roads of Smugglers’ Notch, where sheer rock walls and colorful mountain forests create one of Vermont’s most iconic drives.
Later in the afternoon, enjoy free time in Stowe village for browsing boutiques, sampling Vermont maple treats, and photographing covered bridges tucked into quiet country lanes.
Outdoor enthusiasts may opt for an easy walk at Trapp Family Lodge, made famous by The Sound of Music, offering panoramic mountain views and well-maintained meadow trails.
Our afternoon concludes with a scenic drive
through the surrounding countryside before heading toward our overnight accommodation, The Stoweflake Mountain Resort & Spa.
Day 2: October 5, 2026
White Mountains and Conway Scenic Railway
After breakfast, we depart Vermont and travel east into New Hampshire’s White Mountains region, one of New England’s most dramatic mountain landscapes, where narrow passes, granite peaks, and rushing waterfalls define the scenery. Upon arrival, our guide will lead us through Franconia Notch State Park, an awe-inspiring mountain corridor flanked by towering cliffs
and dense forests ablaze in autumn color.
Time permitting, enjoy short walks to The Basin, a naturally carved granite pool with cascading water, or explore Flume Gorge, a wooden pathway winding through towering rock walls and waterfalls. These gentle walks allow us to enjoy the sights without strenuous hiking. A stop in North Conway provides time for lunch, village strolling, and shopping in one of New
Hampshire’s most popular mountain towns.
In the afternoon, board the Conway Scenic Railway for a nostalgic rail journey through the Mount Washington Valley. Traveling along the Saco River and through forested landscapes, this heritage train ride offers one of the region’s best leaf-peeping experiences from the comfort of a beautifully restored railcar.
Later in the day, we’ll continue south toward Portland, Maine, following scenic byways through rural New Hampshire before reaching the Atlantic coast, where we will stay for 2 nights.
Day 3: October 6, 2026
Wells, Kennbunkport Cruise and Portland
Today begins along Maine’s beautiful Atlantic coastline as we depart Portland and head south to explore some of the state’s most scenic seaside Communities. Leaving the city behind, we’ll follow coastal byways through salt marshes, fishing villages, and forested inlets before arriving in Wells, Maine.
Known for its wide sandy beaches, tidal marshes, and abundant birdlife, Wells
offers a relaxing introduction to Maine’s quieter coastal charm. Time permitting, enjoy
a brief seaside stop or walk along the shoreline, where panoramic ocean views and
crisp sea air set the tone for the day.
From Wells, continue north to Kennebunkport, one of Maine’s most iconic harbor towns, famous for its historic sea captain homes, lobsterboats, and working waterfronts. Here, we’’ll enjoy a scenic coastal cruise exploring
protected bays and rocky shoreline, with chances to spot lighthouses, seabirds, and
seals while learning about the area’s maritime heritage. Before or after our cruise, enjoy free time in Dock Square to browse boutiques, relax at harborfront cafés, and sample classic Maine seafood.
In the afternoon, return to Portland (approx. 45 minutes), Maine’s largest city and cultural hub. Spend time exploring the Old Port district with its cobblestone streets, brick warehouses converted into shops and galleries, and bustling waterfront atmosphere. Optional light walking includes the Eastern Promenade Trail for ocean views or a visit to the iconic Portland Head Light if timing allows.
Our day concludes back in Portland, where our guide will assist with hotel return at the Portland Regency Hotel.
Day 4: October 7, 2026
Departure for Separate Bike Tour
Check out of the hotel at the appropriate time or standard hotel check out time.
