An 8-Day Fall US NE Roadtrip: Fall Leaves, Vermont Bridges, Adorable Towns & Beautiful Drives

My husband and I were celebrating our first wedding anniversary and flew from Denver to Boston, landing around 2 pm, rented a car and drove to our hotel (Ritz Carlton). Upon check-in, we quickly settled in and walked over to North End to stand in line for Neptune’s Oyster for dinner. It was a Friday night and they do not take reservations, so we got in line around 4:45 pm and sat about 45 minutes later. This dinner was absolutely delicious—everything from the scallops to the oysters to the drinks and dessert. Highly recommend Neptune’s Oyster if you have a small party for dinner or brunch. We walked back to our hotel after dinner to enjoy some cards and drinks at Avery Bar in the Ritz Carlton.

We woke up in Boston, MA, at the Ritz Carlton. Enjoyed breakfast at the hotel and then set out on the Freedom Trail—I recommend downloading a map with some brief explanations of all the stops. We made it to Copp’s Hill Burying Ground before turning back to the hotel, not before we enjoyed a beverage at Sam Adam’s Brewery.

Upon packing up and heading out of Boston, we drove US 1 north towards Salem, MA. We attempted to stop for lunch in Salem, however due to it being the first weekend in October, the town was really busy and we could not find parking after one hour of searching. October and Halloween are huge in Salem, so if crowds are not your thing, then I recommend you not visit Salem in the month of October. We continued our drive to Portsmouth, NH, where, upon check-in, we enjoyed a delicious dinner at The Surf Room (very crowded and recommend reservations) before wandering around Portsmouth. It was a beautiful town, we stayed at the Sheraton Harborside and loved being close to the water.

We set out from Portsmouth, NH with PSLs and beautiful weather. We drove north up US 1 and saw a ton of lighthouses: Cape Neddick—Nubble Lighthouse, Cape Elizabeth—The Port Head Light, and a few others. We loved seeing these lighthouses and driving along Shore Drive (Ogunquit) and US1. We stopped at All Points Fly Shop so we could get a fishing license and learn about Maine fly fishing. We had lunch in Fort Williams State Park at Bite Into Maine, touted as the best lobster roll in Maine; these exceeded our expectations! We highly recommend stopping at Bite Into Maine if you are doing this roadtrip. After, we continued north to Bar Harbor and checked into our hotel before a great dinner at La Bella Italian. We wanted to stop at the Visitor Center in Acadia on our way into Bar Harbor, however due to US Government shutdown we decided against it. We loved our first night in Bar Harbor.

Today was sunrise at Cadillac Mountain, so we woke up super early, grabbed our coffee, breakfast, and water, and drove out to Acadia National Park. We were at the top of Cadillac by 5:30 am (sunrise was at 6:30 am). It was beautiful and so incredible. Make sure you get your reservation early and are aware of ticket entrance timings. Even though the US Government was shut down, they still had rangers checking tickets and allowing permitted cars up the mountain.

After sunrise, we headed out to Jordan Pond, which was beautiful, serene, and quiet. We fished and hiked around and enjoyed a car-picnic snack (Jordan Pond House does not open until 11 am in the fall, so do not plan to have breakfast up there). After spending time at Jordan Pond, we hopped in the car and drove Park Loop Road to Thunder Hole to see the high tide come in and walk Ocean Path—this is a beautiful area of the park and I highly recommend spending some time on this side.

Midday, we headed back to Bar Harbor to grab lunch and relax/wander downtown. Tonight we had one of our best meals in Bar Harbor—Table Salt. We loved this restaurant—everything from the ambiance to the cocktails to the food. Highly recommend getting a reservation here.

Sunrise round two, but this time on the Ocean Path and with a photographer. It was another early morning but so worth it seeing the sunrise from a different perspective and area of the park. After we finished our shoot at Jordan Pond, we went back to Bar Harbor to grab breakfast, change, and pack up to go for a bike ride on the Carriage Roads. We rented bikes from a shop in downtown and rode from downtown to the park—a pretty easy ride (although there was a hill midway). We rode out to the Witches Ponds then down and around Eagle Lake—it was beautiful, pretty consistent bike traffic, and oh so worth the ride. We did not bike around Jordan Pond due to the distance; from town to Witches Ponds around Eagle Lake and back to Bar Harbor was over 16 miles of biking. There are a lot of e-bike options in Bar Harbor if you are not comfortable or fit enough for a 15+ mile regular bike ride. If you want to go through the entire park and are not in “biking shape”, I highly recommend picking an e-bike option.

Tonight we had dinner at Stewman’s (we needed to get there early to get a table) and it was so delicious—everything from the lobster platter to the lobster salad and blueberry pie.

Today we had a chill day and skipped our Cadillac Mountain reservation since we had spent time there earlier in the week. There were two cruise ships in port, so it was much more crowded than we had all week. We had the best breakfast at Jordan’s Restaurant in Bar Harbor (make sure you get their blueberry muffins and blueberry pancakes—they were the best!), then wandered around town—shopping and exploring the quaint town. We grabbed Lobster Rolls at The Stadium, which were incredible, however, please note that they do not have seating and they only do to-go meals. We took it back to our hotel to enjoy lunch, and they were the best.

Tonight, before dinner, we returned to Table Salt for another round of incredible cocktails (shout out to their PSL Martini and their Old Fashion). We had dinner at The Reading Room to celebrate our anniversary and our last night in Bar Harbor. We had delicious steaks and drinks before walking back to the hotel.

Today we woke up early, and headed southwest to Vermont for our next adventure. We decided to take the long way, seeing the mountain passes and driving through inland Maine and New Hampshire.

Highly recommend driving over Kancamagus Pass in New Hampshire to experience the full fall scenery and the beautiful mountain pass. We arrived in Manchester, Vermont, and stayed at Equinox Golf Resort & Spa—a beautiful old hotel. Manchester is a quaint town in the mountains and also has the American Fly Fishing Museum and Orvis Flagship store.

We had dinner at The Chop House, which was delicious. On Thursdays, they have a date-night deal so you can get an appetizer, two entrees, and a dessert for a really great price. We loved staying at this hotel and will be back again soon.

Today we woke up, had breakfast at the hotel, and set out to visit the American Fly Fishing Museum (houses the world’s largest collection of angling artifacts) and Orvis Flagship store before setting out on another day of a beautiful drive and seeing some of Vermont’s historic bridges. We headed out to Cambridge, NY to have lunch at a delicious burger place (Anita’s Burger Den) and then headed back East to Boston.

We stayed at the Fairmont Copley Plaza hotel, which was incredible! We loved our large room, drinks at the bar, and the location near where we were having dinner. Tonight we had reservations at the Atlantic Fish Company, which had some of the best seafood and dinners throughout the trip. We met some family for drinks after.

The Fairmont Copley Plaza Hotel had one of the best breakfasts of the trip (second to Jordan’s Restaurant).