Our New England Fall Road Trip

Exploring the scenic beauty of the Northeast - September 20-27, 2025

Welcome to our autumn adventure!

We're excited to embark on this 8-day journey through some of the most picturesque destinations in the Northeast. We'll be chasing the fall foliage through New York, Vermont, New Hampshire, and Maine, staying at unique hotels along the way. We'd love to meet up with any friends who happen to be in these areas during our trip!

Starting from our home in Califon, we'll make our way through charming towns, scenic mountain landscapes, and coastal communities during peak foliage season. Below you'll find our detailed itinerary with accommodation information, dining recommendations, and activities for each day.

Detailed Daily Itinerary

Day 1: Friday, September 20 - Califon, NJ

Our journey begins at home in Califon, NJ. We'll be finalizing our packing, checking weather forecasts, and preparing camera equipment for capturing the beautiful fall colors ahead.

Day Schedule:

Morning & Afternoon: Finalize packing and trip preparations
Evening: Host farewell dinner at home
Accommodation: Home Sweet Home

Enjoying our last night at home before the road trip begins!

Day 2: Saturday, September 21 - Califon, NJ to Woodstock, NY

Driving Distance: 211 km (131 miles) | Driving Time: 2 hours 12 minutes

Our first destination is the artistic community of Woodstock, NY, known for its vibrant arts scene, eclectic shops, and gorgeous Catskill Mountain surroundings.

Day Schedule:

9:00 AM: Departure from Califon
10:30 AM: Scenic stop at Delaware Water Gap
12:30 PM: Lunch in New Paltz at Main Street Bistro
2:00 PM: Continue to Woodstock via NY-32 N with stops at Minnewaska State Park and Ashokan Reservoir
3:00 PM: Arrive in Woodstock and check in at Woodstock Way Hotel
Evening: Explore town center and dinner at Silvia Restaurant

Highlights:

  • Explore the charming village center with numerous art galleries
  • Visit Tinker Street for unique shopping
  • Enjoy the beautiful fall colors of the Catskill Mountains
  • Overlook Mountain Trailhead (optional 2-hour hike for panoramic views)
Accommodation: Woodstock Way Hotel

A boutique hotel nestled in the heart of Woodstock, featuring modern amenities with rustic charm and a beautiful stream running through the property.

Visit Hotel Website
Dinner: Silvia Restaurant

Farm-to-table restaurant featuring seasonal, locally-sourced ingredients. Recommended dishes: Wood-fired vegetables, locally-raised meat dishes, craft cocktails.

42 Mill Hill Rd, Woodstock, NY

Day 3: Sunday, September 22 - Woodstock, NY to Lake Placid, NY

Driving Distance: 308 km (191 miles) | Driving Time: 3 hours 7 minutes

We'll drive north to the Olympic village of Lake Placid in the Adirondack Mountains, taking a scenic route through the spectacular High Peaks region.

Day Schedule:

Morning: Breakfast at Bread Alone Bakery
10:00 AM: Check out and optional short hike at Overlook Mountain
1:00 PM: Lunch at Sticks & Stones Wood Fired Bistro (Schroon Lake area)
2:30 PM: Continue north with scenic stops at Schroon Lake, Keene Valley, and Cascade Lakes
5:00 PM: Arrive in Lake Placid and check in at Lake Placid Lodge
Evening: Dinner at Top of the Park or Artisans at the Lodge

Highlights:

  • Stunning views of the Adirondack High Peaks in fall color
  • Scenic drive through Keene Valley, known as the "Home of the High Peaks"
  • Photo opportunities at the beautiful Cascade Lakes
  • Evening relaxation by the lake with mountain views
Accommodation: Lake Placid Lodge

A luxurious Adirondack-style lodge set directly on Lake Placid with handcrafted furnishings, stone fireplaces, and spectacular lake views.

Visit Hotel Website
Dinner: Top of the Park

Rooftop dining with spectacular views. Recommended: Local trout, seasonal specialties, extensive whiskey selection.

2407 Main St, Lake Placid, NY

Day 4: Monday, September 23 - Lake Placid, NY to Stowe, VT

Driving Distance: 150 km (93 miles) | Driving Time: 2 hours 28 minutes

We'll cross into Vermont to visit the picturesque town of Stowe, famous for its ski slopes and spectacular fall foliage. The drive takes us through the beautiful Green Mountains.

Day Schedule:

Morning: Breakfast at the Lodge or Origin Coffee Co.
9:00 AM: Visit Olympic Center and Museum
11:00 AM: Check out and lunch at Big Slide Brewery & Public House
1:00 PM: Depart for Stowe with stops at High Falls Gorge and Smugglers Notch
4:00 PM: Arrive in Stowe and check in at Trapp Family Lodge
Evening: Explore lodge grounds and dinner at Plate Restaurant

Highlights:

  • Olympic history and mountain views in Lake Placid
  • Scenic drive through Vermont's Green Mountains
  • Dramatic rock formations at Smugglers Notch mountain pass
  • European alpine ambiance at the Trapp Family Lodge
Accommodation: Trapp Family Lodge

A European-inspired mountain resort owned by the von Trapp family of "The Sound of Music" fame, with stunning mountain views and Austrian-inspired architecture.

Visit Hotel Website
Dinner: Plate Restaurant

Upscale dining with locally-sourced Vermont ingredients. Recommended: Seasonal tasting menu, craft cocktails, and artisanal cheese plates.

91 S Main St, Stowe, VT

Day 5: Tuesday, September 24 - Stowe, VT to Bretton Woods, NH

Driving Distance: 138 km (86 miles) | Driving Time: 1 hour 48 minutes

We'll journey east to the White Mountains of New Hampshire, taking the scenic route through Smugglers Notch and stopping at Zenbarn for a late lunch or early dinner.

Day Schedule:

Morning: Breakfast at Trapp Family Lodge
9:00 AM: Take the Auto Toll Road up Mount Mansfield or visit Moss Glen Falls
11:00 AM: Check out and optional light lunch at Piecasso Pizzeria
1:00 PM: Depart via VT-108 through Smugglers Notch
2:00 PM: Stop at Zenbarn in Waterbury Center for lunch/early dinner
4:30 PM: Arrive in Bretton Woods and check in at Omni Mount Washington Resort
Evening: Explore the historic resort and relax on the veranda

Highlights:

  • Panoramic mountain views from Mount Mansfield
  • Dramatic winding road through Smugglers Notch Pass
  • Farm-to-table cuisine at Zenbarn in Waterbury Center
  • Historic grandeur of the Omni Mount Washington Resort
Accommodation: Omni Mount Washington Resort

This grand historic hotel dates back to 1902 and offers luxury accommodations with stunning views of Mount Washington and the Presidential Range.

Visit Hotel Website
Lunch/Early Dinner: Zenbarn

Farm-to-table restaurant with a casual vibe. Recommended: Vermont craft beers, grass-fed burgers, creative vegetarian options.

179 Guptil Rd, Waterbury Center, VT

Day 6: Wednesday, September 25 - Bretton Woods, NH to Kennebunkport, ME

Driving Distance: 159 km (99 miles) | Driving Time: 2 hours 20 minutes

We'll head to the coast of Maine to experience the charming seaside town of Kennebunkport, with its beautiful harbor and New England coastal charm.

Day Schedule:

Morning: Breakfast at the resort
9:00 AM: Mount Washington Cog Railway or drive part of the Kancamagus Highway
11:00 AM: Check out from resort
12:30 PM: Lunch at Delaney's Hole in the Wall in North Conway
2:00 PM: Drive to Kennebunkport with stops at Portland Head Light and Cape Elizabeth
4:00 PM: Check in at Kennebunkport Inn
Evening: Explore Dock Square and dinner at The Clam Shack

Highlights:

  • Mountain views and fall colors in the White Mountains
  • Iconic Portland Head Light lighthouse
  • Beautiful rocky coastline at Cape Elizabeth
  • Charming harbor town of Kennebunkport
Accommodation: Kennebunkport Inn

A historic inn located in the heart of town, offering New England charm and within walking distance to shops, galleries, and restaurants.

Visit Hotel Website
Dinner: The Clam Shack

Award-winning lobster rolls and seafood. Must try: Lobster roll with butter or mayo (or both!).

Day 7: Thursday, September 26 - Kennebunkport, ME to Woodstock, VT

Driving Distance: 254 km (158 miles) | Driving Time: 2 hours 35 minutes

We'll head back inland to visit Woodstock, Vermont, often called one of America's prettiest small towns, especially beautiful in fall.

Day Schedule:

Morning: Breakfast at the inn or Mornings in Paris coffee shop
9:00 AM: Scenic drive along Ocean Avenue with stops at Walker's Point and Goose Rocks Beach
10:30 AM: Check out and begin drive west
12:30 PM: Lunch at Row 34 in Portsmouth, NH with time to explore the historic downtown
2:00 PM: Continue west with scenic stops at Lake Winnipesaukee and Quechee Gorge
4:30 PM: Arrive in Woodstock, VT and check in at Woodbridge Inn
Evening: Explore town center and dinner at The Prince & The Pauper

Highlights:

  • Maine coastal scenery along Ocean Avenue
  • Historic seaport of Portsmouth, NH
  • Vermont's "Little Grand Canyon" at Quechee Gorge
  • Quintessential New England village of Woodstock
Accommodation: Woodbridge Inn

A charming inn located in the heart of Woodstock offering comfortable accommodations in a historic setting.

Visit Hotel Website
Dinner: The Prince & The Pauper

Upscale dining with seasonal menu. Recommended: Vermont cheese plate, locally-raised meat dishes.

Day 8: Friday, September 27 - Woodstock, VT to Peekskill, NY

Driving Distance: 380 km (236 miles) | Driving Time: 4 hours

For our final day, we'll head south to the Hudson Valley town of Peekskill, NY, enjoying the scenic Taconic Parkway along the way.

Day Schedule:

Morning: Breakfast at the inn or Mon Vert Café
9:00 AM: Visit Billings Farm & Museum or shop for Vermont specialty products
10:00 AM: Check out and begin drive south
12:30 PM: Lunch at The Silver Fork in Manchester, VT
2:00 PM: Continue south via Taconic State Parkway with scenic stops along the way
4:30 PM: Arrive in Peekskill and check in at The Abbey Inn
Evening: Dinner at 1915 Restaurant at Bear Mountain Inn

Highlights:

  • Vermont farm heritage at Billings Farm & Museum
  • Shopping and dining in Manchester, VT
  • Scenic drive along the Taconic State Parkway
  • Stunning views of the Hudson River
Accommodation: The Abbey Inn

A boutique hotel set in a former convent with panoramic Hudson River views, featuring luxurious accommodations and fine dining.

Visit Hotel Website
Dinner: 1915 Restaurant at Bear Mountain Inn

Historic dining room featuring American classics. Recommended: Seasonal game dishes, hearty comfort food.

Bear Mountain, Tomkins Cove, NY

Our New England Fall Road Trip Route

Follow our journey through New Jersey, New York, Vermont, New Hampshire, and Maine with this interactive map. Click on any marker to see details about each stop.

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Trip Route Overview

  • Day 1: Califon, NJ (Start)
  • Day 2-3: Woodstock, NY
  • Day 4: Lake Placid, NY
  • Day 5: Stowe, VT
  • Day 6: Bretton Woods, NH
  • Day 7: Kennebunkport, ME
  • Day 8: Return to Califon, NJ

Fall Foliage Forecast for September 2025

Based on historical data and climate patterns, here's what to expect for fall colors during our trip:

Adirondacks & Northern Vermont (Sep 22-23): Early peak to peak conditions (90-100% color)
White Mountains, NH (Sep 24): Early peak conditions (80-90% color)
Coastal Maine (Sep 25): Early color development (40-60% color)
Central Vermont (Sep 26): Near peak conditions (70-90% color)
Hudson Valley, NY (Sep 27): Early color development (30-50% color)

This timing places us perfectly to catch the progression of fall colors from north to south!

New England Fall Travel Tips

Weather Preparation

Fall weather in New England can be highly variable. Pack layers, as temperatures can range from warm days (60s-70s°F) to cold nights (30s-40s°F), especially in mountain areas.

Always bring a waterproof jacket, as rain showers are common in autumn.

Photography Tips

Morning light provides the richest fall colors - plan to be at scenic overlooks early.

Overcast days can actually enhance color saturation in photos, so don't be discouraged by cloudy weather.

Bring polarizing filters to reduce glare and enhance foliage colors.

Scenic Byways

Consider these officially designated scenic routes for the best views:

  • Kancamagus Highway (NH) - One of America's most scenic drives
  • Green Mountain Byway (VT) - Beautiful route through Stowe area
  • Mohawk Trail (MA) - Historic scenic route
  • Crawford Notch (NH) - Spectacular mountain pass

Local Specialties

Don't miss these regional foods:

  • Fresh apple cider and cider donuts
  • Maple syrup and maple products
  • New England clam chowder
  • Maine lobster rolls
  • Vermont cheese

Road Conditions

Mountain roads like Smugglers Notch can occasionally close due to early snow or ice - check conditions before travel.

Some scenic roads get very busy during peak foliage weekends. Start early to avoid crowds.

Best Viewpoints for Photos

Our top recommendations for fall photography:

  • Overlook Mountain Fire Tower (Woodstock, NY)
  • Whiteface Mountain Veterans Memorial Highway (Lake Placid)
  • Smugglers Notch Pass at sunset (Stowe)
  • Artists Bluff (Franconia Notch)
  • Ocean Avenue (Kennebunkport)
  • Quechee Gorge Bridge (Woodstock, VT)

Rainy Day Alternatives

In case of inclement weather, here are some indoor activities for each destination:

Woodstock, NY Area

  • Woodstock Artists Association & Museum
  • Art galleries on Tinker Street
  • Catskill Mountain Pizza Company (cozy indoor dining)

Lake Placid Area

  • Olympic Museum
  • The Wild Center in nearby Tupper Lake
  • Lake Placid Center for the Arts

Stowe Area

  • Vermont Ski & Snowboard Museum
  • Ben & Jerry's Factory Tour (nearby)
  • Stowe Cider tasting room

White Mountains Area

  • Spa day at the Omni Mount Washington Resort
  • Mount Washington Hotel history tour
  • North Conway shopping outlets

Weather Forecast for Our Trip

Check the current forecast for each destination on our journey. Weather data is provided by OpenWeatherMap and is updated regularly.

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