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Thinking of taking a road trip this fall? I’ve rounded up my top 5 destinations you have to visit in the Northeast, with my favorite dining and entertainment rec’s, too. Thank me later 😉
TL;DR?
5. Burlington, VT
4. Woodstock, VT
3. Portsmouth, NH
2. Portland, ME
1. Hawley, PA
If the last 18 months have taught me anything, it’s that you don’t have to board a plane (or even drive that far) to feel like you’re on vacation. In fact, while most vacations I’ve been on are planned months in advance, some of my favorite have been quickie road trips planned just a few weeks ahead of time! I am not a spontaneous person, so these trips were a *big deal*.
In the spirit of the best season ever, Autumn, and taking full advantage of the foliage changing, I’ve rounded up my top 5 road trip destinations in the Northeast that you can take – this weekend! Since I live in Southern CT, all travel times will be from that starting point with driving as the mode of transportation. Depending on where you live, they can obviously look different for you.
5. Burlington, Vermont
Driving distance from New Haven, CT: 273 miles
Last October, we took a road trip up to Burlington for our anniversary. Leaf peeping in CT is lovely, but WOW Vermont really takes it to a new level. We lucked out and got to visit right around peak foliage and as an eternal fall lover it was truly magical. Honestly its worth the drive up there just for the foliage.
Things were very limited given the global pandemic, but we were still able to see and do lots on our weekend trip! Our first stop was the Church Street Marketplace. Closed to traffic, the area is filled with cute shops and fun local eateries. Our biggest rookie mistake was forgetting that everywhere needed reservations, but we lucked out and got outdoor seating at RiRa. Its not local but it is delicious.
We also made our own little brewery tour through the city – including Foam Brewers, Zero Gravity, Citizen Cider, and Queen City Brewery. We got to-go growlers at Foam, lunch at Zero Gravity, and Dinner at Citizen Cider. It was a fun way to spend a day (almost all of them were walking distance from each other) and we got to eat some very yummy food and drink even yummier beers/ciders in the process.
Since the weather was so nice, we walked along the shores of Lake Champlain and stopped in coffee shops and bakeries for snacks. My favorite (and apparently everyone else’s too) was a place called August First. It’s a very unassuming building but the bakery was very legit. We stumbled upon it on our walk and the line told us we needed to try it. They closed a street down to put out seating!
Overall I was thrilled with how kid friendly most places were, and the walkways along the water were a definite highlight of the trip. Its literally miles of beautiful views and little parks everywhere.
Highlights:
Dining:
-RiRa
-August First
Breweries:
-Zero Gravity (awesome food)
-Foam Brewers
-Queen City
-Citizen Cider (awesome food)
Attractions:
–Church St Marketplace
-Lake Champlain
–Waterfront Park (paved trails)
4. Woodstock, VT
Driving Distance from New Haven, CT: 187 miles
On our way home from our Burlington road trip, I convinced my husband to stop at this little town I saw someone rave about while I was planning our weekend. Woodstock, VT was just barely out of the way and SO WORTH IT. Apparently we weren’t the only ones with this detour in mind. though. It was bumpin’ with out-of-towners and leaf-peepers alike. The main road is so pretty it looked fake. Old brick buildings with tons of history, beautiful homes fully decorated for fall, and the quaintest little shops you’ll ever see. There is a covered bridge right off the main road that was a perfect fall photo op too! I’m telling you I still am undecided if the whole place was a figment of my fall loving imagination.
We (of course) found a cute coffee shop called Abracadabra Coffee Co which butted up against a stunning river front park. We enjoyed our coffees while our daughter ran through the grass before we hit the road again. It was 100% the perfect way to end the road trip. Next time we visit, I fully plan on making it an overnight stop.
Highlights:
Dining:
-Abracadabra Coffee
Attractions:
–The Green (Historic District and Homes)
-Middle Covered Bridge (Photo Op)
-Town Center (adjacent to the green, shopping)
-East End Park (riverfront park, next to Abracadabra)
3. Portsmouth, New Hampshire
Driving Distance form New Haven, CT: 186 miles
My husband and I came to Portsmouth for our 1st wedding anniversary. Our first stop was actually the outlets which, while only a 5 minute drive from Portsmouth, are in Kittery, ME. The weather was not what we packed for and had to buy some extra layers.
Portsmouth is a perfect walking city. We parked at our hotel and didn’t need to get our car again until we were leaving. Mid-October is such a nice time to visit; with warm days and chilly nights you really get the best of both worlds. I loved all the cobblestone streets and historic sections to explore!
We walked to the Strawberry Banke Museum and the neighborhoods surrounding, and then weaved our way through different streets until we reached Market Square – what’s considered the main section for shopping and eating.
Each time we road trip to a new place, we always find ourselves on a self-guided brewery crawl. Our first stop was in Market Sq – Portsmouth Brewery. We also visited Liar’s Bench and Great Rhythm – both close by on paper but kind of a trek walking… Learned that the hard way 😅. Liar’s Bench was a cool little spot with very tasty beers and even better merch. Great Rhythm was along a river (creek?) and had awesome views to soak in while enjoying your drink. They also had a nice selection of kombucha which was a pleasant surprise. We also stopped at White Heron Coffee on the way back for an energy boost.
If you’re going to have one nice meal, make a reservation at Surf. Its right on the water and has an amazing menu. The calamari there is some kind of magic, and I’m not a big clam chowder fan but again… magic. A little spendy but worth every penny!
Highlights:
Dining:
-White Heron Coffee
-Surf
-Legends Tavern (pool hall)
-The Friendly Toast (amazing brunch)
-Popovers on the Square
Breweries:
-Portsmouth Brewery
-Liar’s Bench
-Great Rhythm
Attractions:
-Strawberry Banke Museum
–Market Square (shopping, dining hub)
–Outlets in Kittery, ME (5min drive)
2. Portland, Maine
Driving distance from New Haven, CT: 236 miles
The first time I visited Portland was on my Bachelorette. None of us had ever been, but according to the internet it was a great place for girls trip.
The internet was right.
We stayed in Old Port, which was the hotspot for things to do. It was mid September, the weather was perfect and we had the best time. Such a good time, in fact, that I booked a weekend road trip for my husband and I to visit the week after our wedding! Same hotel and everything 😂
Old Port is such a pretty section of the city. Its right on the water, lined with cobblestone streets, and filled with the best shops and restaurants around. Our very first stop (before we valeted the car for the weekend) was Allagash Brewery. We took the tour and spent some time enjoying the pretty outdoor space on the property.
If the trend hasn’t been clear yet, our top priorities in new cities are basically eating great food and finding cool spots to drink. Bonus points if we can do both at the same time! There are lots of different dining options depending on what your budget and preferences are. One of the nights we ate at DiMillo’s on the Water which is literally a restaurant boat! The food was great and the experience was also one to remember.
We visited the first weekend in November, and decided to take the 20 minute ferry to Peak’s Island. Because it was “off-season” the island was extremely quiet, so we rented bikes and rode around the whole thing! The views were incredible, and there’s one section where the waves wash over smaller stones and it makes the most relaxing sound you could imagine. We sat on a bench and listened to it for a while before moving on. There’s also an old military fortification called Battery Steele tucked away on the island. You can walk around and explore it, although it gives off some horror film vibes.
Back on the mainland, we continued our hunt for food and drink. We hit several other breweries, including Liquid Riot Bottling Company (which is also quite a fun place to eat), Shipyard Brewing Company, Sebago Brewpub, and Vena’s Fizz House, which is an artisanal soda fountain and cocktail bar (!!). Gritty McDuff’s, Andy’s Old Port Pub (fish and chips are a must), Petite Jacqueline’s, Bard Coffee, and Central Provisions were all delicious stops.
As a final farewell we stopped at Holy Donuts. If you know what’s good for you, you’ll wait in line to get some. YUM!
Highlights:
Dining:
-DiMillo’s on the Water (a boat!)
-Gritty McDuff’s
-Andy’s Old Port Pub
-Petite Jacqueline’s (amazing brunch)
-Central Provisions
-Elevation Burgers
-Bard Coffee
-Holy Donuts
Breweries:
-Allagash
-Liquid Riot (great food)
-Shipyard
-Sebago (also a restaurant)
-Vena’s Fizz House (cocktail bar)
Attractions:
-Old Port (shopping and dining hub)
–Peaks Island
-Battery Steele (on Peaks Island)
1. Hawley, Pennsylvania (Woodloch Pines Resort)
Driving Distance from New Haven, CT: 141 miles
For my forever number one pick – Woodloch Pines. Not a city like all my previous road trip stops, but packed with so much to do it won’t matter. Tucked away at the base of the Pocono Mountains is this resort geared towards families, with daily activity sheets jam packed with fun things to do.
Our traditional visit is over the 4th of July every year with all my extended family, but I have also been on smaller trips in the winter as well. I cannot stress enough how magical this place proves to be in all types of weather.
Things to do
Before I was a mom, filling my days with as many organized activities as possible was my M.O. Pool games in the morning, watching the guys play 4 on 4 volleyball tourneys at lunch, and trap shooting in the afternoon was a good day. Then on to a night filled with amazing food from the Dining Room and some evening entertainment in the form of live music, a broadway style production, or comedian. If there happened to be any “down time” you could find me on a paddle board in the lake or sipping a cocktail by the outdoor pool.
My days now are a little slower paced, but still so fun. We get to the on-property lake nice and early, hit the playgrounds and mini golf, then go for a dip in one of the incredible little kid water parks. And this is all without leaving the lake!
Woodloch even hosts organized games for younger kids. My daughter is still too young for them, but trust we will take full advantage when she can participate.
They also have bumper boats AND bumper cars, an indoor play gym/obstacle course called The Forest, an outdoor rock wall, zip lining, go-carts, a nature trail, a year-round ice skating rink, and so many more fun things to try out.
Dining
This is arguably the best part about our trips to Woodloch. They have a Dining Room instead of a traditional restaurant where you can choose to have your meals. Meals come included in the price of your stay, and the food is amazing. The menu changes every day, but the wait staff is usually the same for the duration of your stay, so you really get to know them. Since I’m usually with such a large group of people (24 when we can all make it!) dinner is the first time we can all connect and talk about the day/plan out our night.
For instances when you opt to dine elsewhere, they have several other options to choose from. There are some amazing restaurants in Woodloch Springs, which is where their world class golf course and community of guest homes is located. There are also 2 delis, a lakeside bar/snack stand, a sports bar with *the best* bar food, and a coffee shop – all on property.
Bonus Activities
If for some wild reason you feel the need to leave the resort (jk, kinda) there are also fun things to do outside of Woodloch.
Sandwiched nicely between Woodloch Pines and Woodloch Springs is Three Hammers Winery. The first year it was opened I was suuuper pregnant and did not participate in the family outing to visit it, but I made it a point to go the following summer. They offer tastings as well as bottles for purchase and the outdoor seating is so cute. Its surrounded by woods, so it kind of felt like you were in a friend’s backyard enjoying a nice glass of wine. I plan on making it a regular stop on our trips!
If you like antiquing, Downtown Hawley is a hot spot for it. My grandparents always spend at least one day in town shopping for antiques and trinkets to bring home with them. The whole downtown area is so cute with lots of historic buildings and quaint shops and restaurants.
Ski Big Bear is also quite close by. If you visit Woodloch in the winter you can take a day trip to go skiing or tubing and be back in time for a nice dinner in the dining room.
And while I’ve never had the privilege of going, Woodloch has a world rated SPA across the street from Woodloch Springs called The Lodge at Woodloch. If pampering is your thing, this is a must visit. It was recently awarded one of the Top 20 Destination Spas *in the world* by Conde Nast… so, yeah, I feel like that speaks for itself. Its a bucket list visit for me, for sure.
When do we leave?
Writing this post has me itching to go on another road trip now! If I’ve inspired you to hit the road this season, please let me know in the comments! I love hearing how you liked places I recommend. If you’ve been to any of these locations and have some new rec’s, let a girl know! I plan on visiting all of these destinations many more times, so a fresh list of places to see is always welcome. Happy road trip!
