New England Fall 2026

Afternoon: Fly to Boston.

• Southwest flight to Boston Logan (BOOKED)
  • Arrive Boston: 4:30 PM
  • Confirmation: AV54LT
  • Southwest customer service: +1 800-435-9792 (24/7)
• Budget rental car, Boston Logan (BOOKED)
  • Confirmation: 03854260US4
  • Location: Rental Car Center, 15 Transportation Way, East Boston, MA 02128
  • Getting there: after baggage claim, go to the lower-level curb and take the blue Rental Car Center shuttle. It comes every 5–6 minutes.
  • Phone: +1 617-568-6601 (open 24 hours)
  • The car is returned at the Portland, Maine airport on Day 10.

Transport: Drive to Stowe, Vermont, about 3½ hours. Allow an hour for bags and the rental car, so expect to arrive around 9:00–9:30 PM. Most of the drive will be after dark; sunset is around 6:25 PM.

Dinner: Eat dinner on the road. The motel’s restaurant is closed on Wednesdays.

Accommodation: Outbound Stowe (motel) (BOOKED), 876 Mountain Rd, Stowe, VT 05672. Check-in 4:00 PM. Check-out Saturday, October 10, 11:00 AM. Itinerary # 425580192. Phone +1 802-253-7595. Hotel website

Morning: Walk the Stowe Recreation Path, get breakfast, and so on. Then drive up Mountain Road to the Stowe ski area.

• Gondola SkyRide, 2 tickets (BOOKED)
  • Confirmation: 569368239
  • Tickets: pick up at the ticket window
  • Base: 7416 Mountain Rd, Stowe, VT 05672 (map pin)
  • Fall hours: 10:00 AM–4:30 PM, last ticket 4:15 PM, weather permitting
  • Resort phone: +1 802-253-3000

Lunch: 1:00 PM reservation at Cliff House Restaurant (BOOKED), at the top of the gondola. Confirmation TOCK-R-8H36J546; the reservation is in Tock. Your gondola tickets get you there; the lunch reservation does not include the ride. 7231 Mountain Rd, Stowe, VT 05672 (map pin). Phone +1 802-253-3665.

Afternoon: Scenic drive around Stowe: the Jeffersonville – Johnson – Hyde Park loop. Route map

Dinner: At the motel’s restaurant, Eastside Bar + Bites, open 4:00–9:00 PM. Phone +1 802-585-1742.

Morning: Short, easy walks. Pick one or more:

• Moss Glen Falls: 0.5 mile, flat, easy. Hike info · Map
  Parking: a small free lot on Moss Glen Falls Rd. From the village, take Route 100 north about 3 miles, bear right on Randolph Rd, then take the first right onto Moss Glen Falls Rd. The lot is about ½ mile up on the left.
• Smugglers’ Notch Boardwalk / Barnes Camp Boardwalk: 0.2 mile, flat boardwalk. Trail info · Map
  It’s on Route 108 (Mountain Rd) above the ski area. Park in Stowe Mountain Resort Lot D, across the road. The Barnes Camp Visitor Center is open Fri–Mon, 8:00 AM–4:00 PM.

Lunch: Lunch in Stowe village. Walk around the shops.

Afternoon: Go see the covered bridges. Covered bridge guide

Dinner: 7:00 PM reservation at Butler’s Pantry, in the historic Butler House, 128 Main St, Stowe, VT 05672 (map pin). Phone +1 802-253-2955.

Night: The motel’s restaurant and bar are open until 10:00 PM.

Morning: Check out of Outbound Stowe by 11:00 AM. Grab breakfast before leaving town.

Transport: Drive to Rangeley, Maine, through Dixville Notch, New Hampshire. Expect about 3½–4 hours of driving, plus stops. Look at sights along the way.

Lunch: A picnic stop in Dixville Notch at Cascade Brook Picnic Area. Map

Afternoon: Check in from 3:00 PM. Explore Rangeley town and the lake. Rangeley town & lake guide

Dinner: 7:00 PM reservation at Loon Lodge Inn & Restaurant, the dining room at your inn. Dining room info

Accommodation: Loon Lodge Inn (lakeside inn) (BOOKED), 16 Pickford Rd, Rangeley, ME 04970. Check-in 3:00 PM. Check-out Monday, October 12, 10:00 AM. Confirmation # R6529001416. Phone +1 207-864-5666. Inn website

The inn’s doors are locked from 10:00 PM to 7:00 AM.

Morning: Maybe the farmers’ market.

Active options:

• Canoe on the lake. Canoes may be available at the inn; ask at the front desk.

Relaxed options (scenic drives and sights):

• Height of Land: a big lake-and-mountain overlook, a pull-off on Route 17 about 10 miles south of Oquossoc. Map
• Coos Canyon: waterfalls on the Swift River along Route 17 in Byron, about 30 miles south of Oquossoc. Map
• Whip Willow Farm Scenic Overlook: a view over Rangeley Lake, known for sunsets. It’s on Route 4 about 1 mile south of downtown Rangeley. Map

Height of Land and Coos Canyon are both on Route 17, so you can do them as one drive. If you skip Height of Land today, you can stop on the way to Bar Harbor tomorrow.

Dinner: Nothing planned yet. The Loon Lodge dining room is closed on Sundays, so plan to eat in town.

Accommodation: Loon Lodge Inn (second night).

Morning: Check out of Loon Lodge by 10:00 AM.

Transport: Drive to Bar Harbor. Expect about 4 hours of driving, plus stops. You can’t check in until 3:00 PM, so there’s no rush.

• Stop at Height of Land if you didn’t yesterday. Map
• Smalls Falls: a rest area with picnic tables and falls on Route 4, about 12 miles south of Rangeley. Map

Lunch: Lobster roll at Eagles Nest Restaurant, 1016 N Main St, Brewer, ME 04412 (map pin). Open 11:00 AM–7:00 PM. Phone +1 207-989-7635.

Afternoon: Check in at 3:00 PM.

• Acadia National Park vehicle pass (BOOKED)
  • Order #: 0840361062
  • Pass ID: 4DM5FQWF5KG46IALOA
  • Reservation: 0840361062-1
  • Bought on Recreation.gov. The pass must be visible through the windshield. Cell service in the park is very limited, so print it and leave it on the dashboard.

Dinner: 7:00 PM reservation at The Chart Room, 565 Eden St, Bar Harbor, ME 04609. Phone +1 207-288-9740. Restaurant website

Accommodation: The Bayview (hotel) (BOOKED), 111 Eden St, Bar Harbor, ME 04609. Check-in 3:00 PM. Check-out Thursday, October 15, 11:00 AM. Confirmation # 1093492470. Phone +1 207-288-5861. View booking · Hotel website

Morning: Hotel breakfast.

• Carriage ride, Acadia by Carriage (BOOKED)
  • Starts: 9:30 AM. Be there by 9:00 AM.
  • Booking #: 374901392
  • Location: Wildwood Stables, 49 Dane Farm Rd, Mount Desert, ME 04660, just off the Park Loop Road. Allow about 20 minutes to drive there from the hotel.
  • Have the park pass on the dashboard.
  • Phone: +1 207-600-7204 · Website

After the ride, drive around the park.

Lunch: Park in downtown Bar Harbor. Grab lunch somewhere, shop, and so on.

Afternoon: Drinks and snacks at Atlantic Brewing Midtown, 52 Cottage St, Bar Harbor, ME 04609 (map pin). Phone +1 207-288-2326.

Dinner: 6:30 PM reservation at McKays Public House, 231 Main St, Bar Harbor, ME 04609. Parking is behind the restaurant, entered from Newton Way. Phone +1 207-288-2002. Restaurant website

Accommodation: The Bayview (second night).

Morning: Hotel breakfast, then drive the Park Loop Road. The Ocean Drive section is one-way. Have the park pass on the dashboard.

• Thunder Hole: between Sand Beach and Otter Cliff, with a roadside parking lot. Map
• Otter Cliff Overlook: just past Thunder Hole. Map

Lunch: Grab lunch in Southwest Harbor.

Afternoon:

• Bass Harbor Head Light: at the end of Lighthouse Rd, off Route 102A in Bass Harbor. The parking lot is small. Map
• Acadia Lobster Cruise, 2:00 PM
  • Departs: Dysart’s Great Harbor Marina, 11 Apple Ln, Southwest Harbor, ME 04679 (map pin)
  • Parking: park at West Marine, walk past the marina office to the ramp, and wait under the tent.
  • Aim to arrive by 1:45 PM. Bass Harbor is about 15 minutes from the marina.
  • Bookings are by text message with the captain. You’re confirmed once he texts back with the details. Phone (text only): +1 207-370-7663
  • Lobster on a boat! Bring wine and cups.
  • Website

Evening: Head back to the hotel.

Accommodation: The Bayview (third night).

Morning: Hotel breakfast. Check out of The Bayview by 11:00 AM.

Transport: Drive to Portland, with a stop in Freeport. Allow about 3 hours of driving to Freeport, then about 30 minutes more to Portland Head Light.

Lunch: Stop in Freeport. Eat lunch and shop at the L.L.Bean Flagship Store, 95 Main St, Freeport, ME 04032. Phone +1 207-552-7701.

Afternoon: Portland Head Light, Fort Williams Park, 1000 Shore Rd, Cape Elizabeth, ME 04107 (map pin).

Dinner: Lobster roll at the Cousins Maine Lobster food truck, parked in Fort Williams Park on the north side of Capt. Strout Circle, next to the lighthouse. Phone +1 207-805-8800.

Accommodation: Holiday Inn Express & Suites South Portland (hotel) (BOOKED), 303 Sable Oaks Dr, South Portland, ME 04106 (map pin). Check-in 3:00 PM. Check-out Friday, October 16, 11:00 AM. Confirmation # 81835441. Phone +1 207-775-3900. Hotel website

Morning: Check out of the hotel. The airport is a short drive away.

• Return the Budget rental car, Portland Jetport (BOOKED)
  • Location: 1001 Westbrook St, Portland, ME 04102
  • Follow the airport “Rental Car Return” signs. The counter is next to baggage claim, and the cars are across the street.
  • Open 6:00 AM–midnight. After hours, leave the keys in the drop box at the counter.
  • Confirmation: 03854260US4 · Phone: +1 207-874-7521
• Southwest flight home from Portland (PWM) (BOOKED)
  • Confirmation: AV5Y9B
  • Southwest customer service: +1 800-435-9792 (24/7)