Since it’s National “Plan For Vacation” Day I decided it was the perfect time to blog my solo trip this past fall to New England in October!

I went back and forth on going – it was my first trip since Disney in 2019 (almost exactly two years!) and I was a bit nervous to pull the trigger.  I had so many other plans that I canceled due to the pandemic but I felt that the risk was low and decided to go for it.  I was hitting major burnout with weddings.  2021 was SO busy and I know from past years that these fall solo trips really help reset my brain for the remaining rush of the year.

I ended up spending a week in New England (still wasn’t enough time).  I stayed in Woodstock VT, Gorham NH, Wells ME and Provincetown MA.  It was a LOT of driving but SO beautiful.  I highly, highly, highly recommend everyone take this trip at least once in their lives.  The leaves were unreal and I was lucky enough to see the White Mountains at/close to peak.  Normally by this time of the year they are on the tail end but the warm late summer temperatures kept them hanging on a bit longer!

I hope you enjoy this virtual vacation as much as I did!  It’s a LONG blog post, so sorry!  It got so long I decided to split this into two parts!  This is covering the first few days of the trip (Boston to Woodstock, VT and Woodstock to Gorham, NH).

If you are new here be warned: I am not a foodie, I am not bougie and I’m basic AF.

As I generally do, I flew in to Boston on a direct flight from Cleveland on JetBlue.  I’m still sad Akron Canton Airport decided to nix this route *sad violin* but at least Cleveland isn’t too far of a drive.  The flight was surprisingly uneventful and I nabbed my luggage and picked up my rental car pretty easily.  One thing that always amuses me is that in Boston Enterprise ALWAYS spoils me and I get some fun cars for my trips.  This time it was a BMW 330i.

Originally I was going to meet up with Kristen for lunch but sadly they’d had a direct covid exposure and didn’t want to risk it.  I was sad but totally understood!  Luckily for her it ended up just being allergies but I really appreciated her being honest.  Since our lunch plans were dashed I made do with my favorite thing to visit when in New Hampshire – the rest area liquor store!  The one I decided to pull off at – Hooksett Welcome Center – was even fancier with a food court and a few stores.  Since I’m fancy I got mozzarella sticks for lunch before hitting up the liquor store for some prosecco splits for the trip.  Bonus car shot because my husband always demands these because he is also always amused by my fancy rental cars.

Since my plans had changed I ended up going to Plan B which was visiting some of the New England covered bridges along my route to Woodstock in Vermont.  I’d visited a couple with Gianina in years past but it was enjoyable to go see them again.  It was SUCH a beautiful day and was really the perfect day to photograph bridges.  The blue sunny skies always make me happy.

The first bridge I stopped at was Rowell’s Covered Bridge in Hopkinton, NH.  Getting to these bridges is always an adventure in itself and this one had its location long before the actual bridge, a lucky pause in a parking lot led me to the right location.  I also bumped into a sweet woman and her mom when here – I always meet the kindest people when bridge hunting!  They were from Kentucky and decided they also needed to finally break out and get outside of their state to see the world again after a long covid islolation.  This bridge was completed in 1853 and is one of the oldest left in the state.  It’s in SUCH good condition for this old of a bridge!

I moved along towards Woodstock and the next stop was a rare one – the Contoocook Railroad Covered Bridge!  This is the oldest surviving railroad covered bridge.  It underwent extensive renovations in 2003 and now also have a sprinkler system installed.  Sadly too many of these bridges are burned down so I’m glad they’ve taken steps to mitigate any potential fires.  I loved the Halloween decorations the town of  Contoocook had set up (reminded me of Ogunquit) and had to capture a photo of them.  While I was here I also noticed there were sundogs shining.  It’s silly but whenever I see them I think of my Dad and he’s always close to me on these trips so I also had to take a photo of them as well.

Originally I planned to stop at more bridges but I decided to skip them and get to Woodstock before dark.  I don’t mind driving at night but when I’m traveling I prefer to know where my home base is during the daylight so that I’m not lost when coming back after dinner.

All along the drive to Woodstock I just kept gawping at the leaves.  In Ohio they were still very, very green but they were in full bloom in New Hampshire and it was such a pretty drive!  Once I got into town I had to pull over when I realized I was passing a covered bridge but really was more awestruck by the stunning beauty of the leaves reflected over the Ottauquechee River.  The picture doesn’t do it justice but I’m posting it anyway.  Definitely was a sight worth pulling onto the side of the road to see.

I drove through the adorable town of Woodstock and got checked into my hotel for the next two nights at Sleep Woodstock.  I had bounced around looking at a few different hotels but in the end I decided that for me, it felt safest during these times to have a room I could enter from the outside and the charm of this renovated hotel wooed me.  My room was adorable and while it was small it was absolutely perfect for my needs.  The bed was SO comfy!!  The owners were absolutely lovely and I couldn’t recommend this place more.

When checking in the owner warned me that due to the pandemic the dinner options were VERY limited and unless I had a reservation somewhere I was probably out of luck to dine in anywhere.  Outside of weddings, I have not been dining inside so I hadn’t made any reservations since I wasn’t sure how brave I was going to be on this trip and decided to feel it out as I went.  Since the options were VERY limited I ended up going down to a gas station nearby that they recommended that had a small deli attached and got some chips, cheese and pepperoni and made do with what I had.  I’m so glad I had those mozzarella sticks to tide me over!!  Ha!  These chips were dang amazing so no regrets!

The next morning I woke up and it was a bit dreary and very foggy so I hung at the hotel for a bit waiting for the fog to clear out before heading out.  I had a bunch of places in the area I wanted to visit and wasn’t sure where to begin but in the end I decided to start the furthest from town and work my way back to the hotel.  On the way in I’d drove over the Quechee Gorge which was beautiful so I decided to head back hoping the fog would continue to lift as the day warmed up.  When I say warmed up, I’m not talking just the sun.  It was over 80 degrees this day – October 13 in VERMONT. It still blows my mind how much warmer this trip was then the similar trip in 2018 which was barely above freezing for the same dates.

I started at Quechee Gorge on the north facing side of the bridge while the fog was just beginning to lift.  I saw a bunch of people coming up the trail and the photos were making me happy so I decided to go see if I could get a view of the bridge from below in the gorge.  I walked down and decided to go downhill so I could hopefully get the fog in the photo as well.  About midway down the STEEP hill I started talking to someone coming back up and they said that the view from the bottom wasn’t really great and not worth the strenuous hike.  I decided to take their advice and turn around.  I later looked up photos and apparently to get the good photos you need to go in the river and I’m glad I turned around given I didn’t have a lot of days to explore.  If I ever go back, I’ll make sure to take enough time to do the trip.

From there I continued over to Quechee, VT to the Quechee Covered Bridge.  While this darling covered bridge isn’t as historic (it was built in the 1970s) it is still picturesque and a pretty bridge over the falls.  It was washed away in 2011 during the flooding from Hurricane Irene but it was restored and reopened.  It’s next to the Simon Pearce store which is super popular given how full the parking lot was!  I was going to pop in but I know myself and that me traveling with anything glass would end in disaster.

From here I decided to drive to the “Instagram Famous” spot in Woodstock – the Sleepy Hollow Farm.  It’s up in the mountains and a bit of a drive but the drive was beautiful.  I couldn’t help but stop and photograph a few views along the way that caught my eye including this random farm, a man riding his bike and other spots along the way.  I cannot express how pretty this drive was!

Finding Sleepy Hollow Farm isn’t too difficult.  You will know you are there when you see all of the cars.  I was not remotely prepared for how many people would be at this spot.  When coming up to it, a neighbor was out blocking off his driveway with flags and cones – that’s how bad it is. This place was made popular due to a photo from KJP (note this is heavily photoshopped) and was recently purchased and is undergoing some renovations.  They have taken down the split rail fencing and painted the house but it’s still a pretty spot.

However, THIS IS SO PHOTOGRAPHER OF ME, the light wasn’t great during my stop.  I kept waffling about it and eventually decided that while it was beautiful and I did take photos I wanted to come back later in the day when the light would be better.  This is why I love solo travel – there’s no one to tell you that this is silly.

You can tell me which time of day you preferred – this was around noon.

I decided that I was finally hungry and drove back to the hotel to change into something a bit cooler as the temps were heating up and to get lunch next door at Mountain Creamery.  It hit the spot and I’m still sad I didn’t get to go back for breakfast the next day.   I headed back out and made my first stop at the nearby covered bridge, Lincoln Covered Bridge.  This was built in 1877 and while it’s pretty it’s less picturesque than the others near/around Woodstock.

As I headed towards town I decided to make a detour and stop at the Woodstock Farmer’s Market and stock up on some food for dinner since I didn’t have reservations for dinner.  There were only about 3 restaurants open for dinner and they were all fully booked.  I ended up getting a variety of things including a pumpkin whoopie pie (DELISH) and some nibbles.  It was such a delightful store!

I finally stopped in downtown Woodstock proper and meandered around a bit.  It was SO busy it was kind of shocking.  Usually when I travel after mid-October the crowds have died down so it was weird to see everything so busy!   I didn’t have a ton of change on me so I ended up leaving a bit earlier than I wanted.  Hopefully I return someday and get to enjoy the town more.  While there I visited Middle Covered Bridge.  This bridge was built in 1969 to replace an iron bridge that was condemned.

I then headed back to Taftsville Covered Bridge for some proper photos.  It was another busy spot with SO many photographers and a couple photo shoots taking place.  I know for most it won’t make sense but by and far most of my bridge adventures at most have one or two other groups there, sometimes a few more in a popular spot.  This was a wild scene for me and I was really surprised.  I should have known the next spot I would go to would be even more busy!  This bridge was built in 1836 (!) and is one of the oldest remaining covered bridges in Vermont and the United States.  This bridge was also damaged by the floods from Hurricane Irene and it took two years to repair.

I decided since the road back to Sleepy Hollow Farm was through the bridge and I was so close I may as well pop back up the mountain to see if the light was any better on the farm.  I was SHOCKED when I pulled up and the place was packed.  When I was there before there was at most about 10-15 people also taking photos.  When I returned a few hours later there was easily 50 or more.  It was absolutely wild and the neighbor looking annoyed and putting up no parking signs began to make sense as cars lined the road. This is not the full reality of how many people were there – just a taste.

I suddenly realized why there was also a gate, cameras and no trespassing signs because people, despite all of this, were walking up and down the road for photos of them with the view behind.  I cannot imagine what it would be like to live here and have this at your gate daily.

On the other side of me in the photo below was another huge setup of cameras on tripods.  I have never seen something like this in the wild before!

Anyway – back to the actual views.  I’m so glad I went back despite the crows as the light was much more even.  I did stay to the road and behind the gate unlike some… Ha!

The next morning I woke up pretty early to set out for the White Mountains after breakfast at the Mountain Creamery.  Unfortunately there was a terrible accident and that plan wasn’t meant to be.  Someone’s car was hit when pulling out of the restaurant and the road was shut down.  The person hit was a regular customer and it wasn’t the time to go to the restaurant.  I hope the person made it through, life flight had to land on the road.

Eventually the stopped cars were able to make a hole for me to nudge out and I was able to head on my way.  The drive was SO pretty along the way to my first stop, another “Instagram” hotspot, Artist’s Bluff Lookout.  Sadly though the further I drove the more the clouds rolled in.  I’m glad that I had the blue skies while I did but I was sad to see them leave.

Note: these photos were taken when I was the only person on the road.  I usually leave my camera with settings that should be right and randomly will aim and shoot at will and hope something comes out whenever it is safe to do so.

I fell in love with the views from Artist’s Bluff Point but I REALLY nervous about attempting it.  I am not a hiker and not in the greatest shape.  I also have asthma which likes to kick off whenever I’m hiking.  Bundle all that with the fact I haven’t been super active since the pandemic started and I was dubious at best to attempt this trail.  While it is short it is basically about a mile straight up from what I read and I wasn’t sure I could do it.

My friend and fellow photographer had recently hiked the Appalachian Trail (he is AMAZING – check out his You Tube here @ Reckless Abandon) and he had hiked this area and it was so beautiful that I had to stop and at least try.

I parked at Echo Lake and took a few photos before giving myself a heck of a pep talk and attempting the hike.  I decided that I would try but gave myself permission to turn around if it was ever too much and take as many breaks as I needed to.  The most scary part at first was finding the dang trail.  You can see it across the street and there is a light path you can see where people climbed up the side of a very steep hill.  I saw someone do it so I went for it.  I learned on the way down that if you go a bit to the right of the entrance to the lot there’s a trailhead with a much easier entrance.  I advise you to do that one LOL.

Look for this sign/trailhead to the right of exiting the RV parking lot at Echo Lake.

This is steeper than it looks!  Don’t make my mistakes and go this way!

There are multiple ways to attack this path.  If you park up at the state park you can take a longer but less dramatic climb in a clockwise direction which also hits the summit of the nearby peak.  If you park where I did you go counter clockwise and climb up the steep side of the mountain.  I chose to come back down the way I went up but many keep going counter clockwise.  If I had more time/the weather was better I would have done this but I’m glad that I went the way that I did.

It is VERY steep to go up but it’s not terribly hard, just taxing.  Take breaks when you need them and step off to the side when you can so others can pass.  From Echo Lake to the bluff it took me about an hour to climb and I stopped pretty frequently to take breaks and drink water.  I’m sure most could make it in less time LOL.  There are plenty trees to grab on to to steady yourself.  It’s a mix of trees/roots and rocks so wear appropriate footwear!

Once I got to the top I could see why it is a popular spot – it is a beautiful view!  Even with the fog and gloomy skies, it was spectacular and kind of just pops up out of nowhere.  The offshoot to get here is somewhat hidden and I had to go through some bushes to get there.  It’s definitely worth the hike and I’m only sorry I didn’t think to bring a lunch to eat up here like so many others did.

As with Sleepy Hollow Farm, this was another popular spot for selfies and I was entertained watching all the people come up and do selfies in the various spots around the lookout.

Going down was a bit more scary but I jokingly told another couple I was going down with that I was “acting like an elderly person with bad knees” and that seemed to do the trick for all of us!  We all made it down without incident.  Once I made it to the car it immediately started pouring and I was glad I had made it just in time!  Going back down the rocks wet would have been scary!

I then drove on into the White Mountains and stopped to take photos of the Omni Mt. Washington Resort overlook.  I’d stopped here before but it was worth stopping again with the leaves still on the trees.  I really wanted to stay here but the rates were $1000 a night.  I didn’t want to stay there THAT bad!  So photos of it would have to do!

I was going to do the cog railroad trip but when I saw that the mountain was socked in with fog I decided to skip it and continue on.  You can see the railroad path to the right of the resort heading into the clouds.

The rain kept sputtering off and on as I continued onward so I skipped some spots that otherwise probably would have been beautiful.  However I did randomly pull in spots that looked interesting and one such spot was Crawford Notch.  When I pulled in there were another gaggle of people staring at the side of the mountain.  I took a photo of the view and then struck up a conversation with one of the photographers.  They were waiting for the Conway Scenic Railroad to pass for photos.  Turned out he was also a wedding photographer and he gave me some tips on where to go the following day.

Just beyond the notch view pull off there were a series of waterfalls alongside the road.  I managed to make the pull off for this one – so pretty!  There were a lot more I wanted to visit but the rain meant that I just saw this one.

I continued along 302 and pulled off again at Fourth Iron Campground which I found to be really a surprise delight!  As a child I did a LOT of tent camping and this location is definitely a place my Dad would have enjoyed.  The iron bride was pretty and the woods surrounding it were also lovely.

I scooted along continuing towards Gorham where I’d be staying for the night but I made one final stop at the Jackson Covered Bridge in Jackson, NH.  This bridge was built in 1876 and is yet another pretty one!

I made it to my home for the night, Town & Country Inn and Resort just as the sun set.  I opted to eat dinner in the restaurant and it was nice to eat indoors again!  While I wouldn’t return to this hotel, it was fine for the night.  The cell signal here is weak and they don’t have much for wifi.  If you want to go off the grid, this is the place to go!  However the timing was terrible because I had quite a few clients trying to book and returning calls and sending out contracts was a bit of a nightmare!