Fall Road Trip Through New England: Where to Go in Maine, New Hampshire and Vermont

See a Lighthouse

Portland, Maine

I flew in and out of Portland for my leaf peeping road trip. As soon as I got my rental car from the airport, I went in search of a lighthouse. The Portland Head Light at Cape Elizabeth is said to be the oldest in Maine. It is also considered the most photographed lighthouse in the country. It’s precariously perched on rocks that look like petrified wood. They get the sparkling glossy look from alternating layers of quartzite and dark grey phyllite.

You can only go inside the lighthouse one day a year, so after I wandered around it, I headed over to the Cousins Maine Lobster food truck and devoured the warm buttery yumminess of a lobster roll. I walked off my late lunch by taking the Cliff Trail for a better view of the lighthouse with the thunderous waves crashing on the rocky shoreline.

Next, I drove over to the Ship Cove picnic area in Fort Williams Park to see some of the military fort ruins and the ruins of one of the first grand houses built along the Cape Elizabeth shore. Completed in 1859 and predating the fort, Goddard Mansion was built of native stone in an Italianate style. In 1900, it was acquired by the United States Army. It was used to house married non-commissioned officers stationed at Fort Williams and later as an NCO (non-commissioned officers) Club until Fort Williams closed in 1962.Six days later, I explored Portland’s waterfront as my last stop of my New England road trip. On that Saturday, the area was buzzing with tourists, including some from a cruise ship. After walking around the wharf, I headed up the uneven sidewalks of Market and Exchange streets in the Old Port district. My favorite store find was Ramblers Way. It’s a family owned clothing store out of Kennebunk. I tried to eat at Eventide Oyster Co. and East Enders but both places were packed. Guess everyone else was hungry for a lobster roll, too. Both eateries were highly recommended to me by locals.

A Quaint Coastal City

Portsmouth, New Hampshire

Portsmouth oozes historic charm everywhere you turn in the downtown area. I did a one-night stay in The Sailmaker’s House. It’s a boutique inn housed in the historic home of a sailmaker named John Holbrook. Renovated in 2017, some of the original architecture dating back to 1801 was preserved, including narrow stairways, original windows and slanted pine floors.

After checking in, I headed to Surf Restaurant with every intention of ordering a piping hot bowl of clam chowder. That was until I saw lobster and Brie nachos on the menu. The Portsmouth food scene quickly surprised me as I savored the decadent nachos paired with a North Country Original Press Cider out of Rollinsford, New Hampshire.

After a restful night, I spent a few hours the next morning wandering around the historic seaport including stops at the African Burying Ground Memorial, Market Square and North Church Congregational United Church of Christ. The congregation started in a log cabin in 1641 and the current church was built in 1855.

I strolled along Commercial Alley then found some retail souvenirs for myself in two fabulous boutiques, Inside Out and Mint Boutique. Then I headed over to the historic Bridge District for a stop in the whimsical brasserie Fezziwig's Food and Fountain in Pickwick’s Mercantile. I ordered a Mr. Fezziwigs's Butter Brew then wandered over to Pickwick’s Mercantile to peruse the gift items.I spent the most time in the 10-acre Strawbery Banke Museum wandering through some of the 32 houses and 10 gardens. My favorites were the penny candy counter in the Little Corner Store and the Goodwin Mansion, the home of the New Hampshire governor during the Civil War which later moved to Strawbery Banke in the 1960s. I took a walk through the flower garden in Prescott Park and looked across to the Portsmouth Naval Shipyard, established in 1800 and still active today.

Along Lake Champlain

Burlington, Vermont

It was dark by the time I got to Burlington for the second night of my road trip. Using my AAA discount, I checked in at the Hilton Burlington. It’s in a fantastic location to explore the waterfront and the historic district.I was in a pizza mood as I walked to the Church Street Marketplace to find a spot for dinner. Sitting at the bar at , I tried a Citizen Cider, the local cider on tap, and a medicine wheel pizza. Since I was in the area where Ben and Jerry’s ice cream started, I splurged and got a cone during my walk back to the hotel.The next morning after admiring the sunrise from my hotel room, I enjoyed the peacefulness of an early stroll on the boardwalk along the shore of Lake Champlain. I had several locals tell me I had to have a Rise & Shiner, and Kountry Kart Deli next to the Flynn Center for the Performing Arts is the place to get one. It’s a grab-and-go deli so I took my breakfast sandwich of egg, cheese and hash browns and sat on a park bench near First Unitarian Universalist Society of Burlington established in 1816. I walked around the vibrant college town for about an hour. Before leaving, I popped into another locals’ favorite, August First Bakery & Cafe. The laptop-free bakery was packed with people sipping coffee and nibbling on baked goods. I grabbed a latte for the road and couldn’t resist one of their coconut almond macaroons.I drove 15 minutes south to Shelburne Farms, a working farm designated as a National Historic Landmark in 2001. I did a 4-mile hike that took me through meadows, forest and along the shore of Lake Champlain. I did take a break mid-hike to explore the gardens of the picturesque The Inn at Shelburne Farms. If you’re looking for a historic and romantic stay near Burlington, this is the place.

Vermont's Little Grand Canyon

Quechee and Woodstock, Vermont

I hadn't planned to spend a night in Quechee or Woodstock, but after making a stop in Quechee on my way from Portsmouth to Burlington, I wished I had. Quechee is where I saw my first Vermont covered bridge over the Ottauquechee River. Seeing the glassblowers at work in Simon Pearce Glass is a must in this charming town surrounded by forest. I was captivated watching them burn and blow votives in the glassblowing studio.

After a night in Burlington, I took a scenic route exploring small towns like Vergennes and Middlebury then cut through the Green Mountain National Forest, an area made famous by poet Robert Frost, just so I could spend a little more time in the Quechee area. I didn’t have time to explore the Marsh-Billings-Rockefeller National Historical Park and it is one of the reasons I want to go back to Woodstock, a quaint town with some stores dating back to the 1800s lining its main street.

My last stop in Vermont was at the Quechee Gorge. Glacial activity about 13,000 years ago created the gorge called “Vermont’s Little Grand Canyon.” You can see the Ottauquechee River flowing 165 feet below the viewing area from the bridge on Route 4.

Highest Peak in the Northeast

Mount Washington and Jackson, New Hampshire

The Wildcat Inn & Tavern is tucked away in the White Mountains in the tiny town of Jackson. With its rustic antique furnishings, the inn is reminiscent of a 1940s ski lodge. Enticed by live Irish music in the tavern, I joined in the fun over a dinner of lobster corn bisque and kale Caesar salad.The next morning, I took a walk around town, including Jackson Pond by the River where I learned that Benjamin Copp and his family settled the town’s first homestead in 1775 at the confluence of the Wildcat and Ellis Rivers. Craving maple syrup, I had a pancake breakfast at , which was home to Arbuckle’s Country Store in the 1950s and 1960s.

Someone at Wildcat Inn told me I had to see Jackson Falls. When I got out of the car, I could only see one section of the falls. I followed a short trail and was amazed by the number of small falls, slides and plunges of different sizes stacked in layers on about a 100-foot stretch of the river. The cascading waterfalls are just a two-minute drive from the inn, so I had no excuse not to go.

On the way to Mount Washington, I stopped at the Honeymoon Covered Bridge, which was built in 1876. Flossie’s General Store near the bridge is worth a stop, too. Mount Washington had been on my radar to visit for a long time. It’s known for the extreme weather conditions it gets, but when I visited, I got 65 degrees and sunny. The harrowing 8-mile drive up the mountain takes you from dense forest to alpine zone. There are pullouts along the road where you can stop on the way up or down. Take advantage of them, especially on the way down to let your brakes cool. At the top, cautiously hike the short and slick Crawford Trail to officially stand on the summit of Mount Washington. At 6,288 feet it is the highest peak in the Northeast.

Acadia National Park

Bar Harbor, Maine

When I got to Bar Harbor, I went straight to Acadia National Park to catch a colorful sunset from Cadillac Mountain. In town for dinner, I walked over to Geddy's Pub for clam chowder and lobster cobb salad. Geddy’s has been around since 1974 and is in a row of restaurants near the harbor. Striking up a conversation with tourists from New York and a few locals, I experienced Bar Harbor’s late-evening scene with stops in Testa's Restaurant and Bar Harbor Beer Works.

I started my full day in Bar Harbor at Slice of Eden Bakery for a latte and bagel. They’re known for their doughnuts. The apple crisp ones looked scrumptious, so I grabbed one for hiking fuel. Instead of doing the traditional 27-mile loop in Acadia National Park, I drove straight to Jordan Pond where I traced the water’s edge on a short hike. Avoiding peak visiting hours in the park, I went out the Stanley Brook entrance and made stops in Seal Harbor and Northeast Harbor, where I grabbed a latte at 123 Café. In the Great Harbor Maritime Museum—housed in an old firehouse dating back to 1917—I learned about Northeast Harbor.

I took the scenic route on Sargeant Drive, which takes you along Seawater Bay in Somes Sound. It’s one of only a few fjords in the contiguous United States. I stopped for lunch in Southwest Harbor. Filled with quaint bed and breakfasts and cute shops, it doesn’t have the hustle and bustle of Bar Harbor. One shop is even called Acadia Quietside. Several locals suggested Beal’s Lobster Pier, a family-owned restaurant on the water since 1932. Sitting in the captain’s galley nook outside, I chatted with a couple from Jacksonville, Florida, between bites of Beal’s traditional lobster roll and sips of a blueberry lemonade.

My next stop was the Bass Harbor Head Lighthouse. Since a Coast Guard family lives in it, you can only tour the outside. I drove back into Acadia National Park and stopped at Pretty Marsh. I walked on the spongy forest floor through the fragrant pines in this secluded southwestern side of Mount Desert Island and ended up at a wooden staircase. I took it down to the shoreline where the afternoon sunshine twinkled like glittery diamonds on the water.

After a quick stop back in Bar Harbor, I drove the 27-mile loop in Acadia National Park since I had about 2.5 hours before sunset. I made a few stops including Thunder Hole and Otter Cliff. My longest stop was at a geological rarity. Sand Beach is one of the few cold-water, shell-based sand beaches in the world. There’s an offshore rock called “Old Soaker.” It diverts a strong current into a glacially formed pocket which catches shell fragments. The cold water then traps gases dissolving the seashells and forming the beach resting on a huge bed of granite stones.I finished the Acadia loop at Cadillac Mountain. The sunset with hues ranging from pink to orange was a stunner even for this perpetual sunset chaser. I chose the upstairs bar in Galyn's Restaurant for a quiet space to sip a dry Ricker Hill Mainiac Gold cider from Maine and enjoy a bowl of traditional clam chowder. On a post-dinner stroll, I stopped in Sherman’s Bookstore, reputedly Maine’s oldest bookstore open since 1886. I looked around Acadia Shop filled with everything from hats to jellies in addition to admiring creations by local artists at Island Artisans, including nautical glass pieces, wool beanies and colorful birdhouses. I thought about tasting the lobster ice cream at Ben & Bill’s Chocolate Emporium, but I opted for a scoop of coffee toffee bar from Bar Harbor’s popular candy shop to end the night.I love a stellar sunrise as much as I love a spectacular sunset. So, before leaving Bar Harbor, I drove back up the 3.5 miles to Cadillac Mountain. I stopped about halfway for an incredible view of fog hovering along the shoreline then raced to the top just in time to hear oohs and aahs from other sunrise watchers as the sun crested the horizon. When I got back into town, I popped into Jordan's Restaurant, a Bar Harbor favorite of locals and tourists. It has great diner coffee and is known for wild blueberry pancakes and muffins. The normal order is two pancakes, but you can order just one as I did and drench it in maple syrup for a Maine delicacy.

On the way out of town, I stopped back in A Slice of Eden for an almond latte for the road. I couldn’t pass up a pumpkin doughnut for later as my fall road trip adventure exploring the history, outdoor adventure and food of New England was coming to an end.

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