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Maple Syrup, crisp air blowing leaves from their resting place. New England is a fall wonderland. New England’s charm and fall festivities keep people venturing to this part of the country year after year.

Grab a suitcase, camera, some plaid, and a sweater for the best way to experience fall – by car.

When my husband and I first started dating we were asked to sing at one of my best friend’s wedding in New Hampshire. I was completely stoked to be asked such an honor. I knew I had to go! I had never been past the New York state line neither had my boyfriend (now husband).

I asked, my adventure-seeking man if he would be down for an epic 5-day roundtrip up north and of course, he said, uhhh yeah!

We loaded up our cameras and my guitar into the back of his 90’s Volvo, with no air conditioner might I add, and headed up I-81.

We blasted fun sing-along songs and made it one big adventure on a budget. Check out our itinerary of the stops we made below for some amazing must-sees!

Ready to experience fall in a fast 24 hours or less in each destination? Let’s go, it’s all about bang for your buck on this trip!

1. Stop in New York City for the evening

Where to go in New York City 

I highly recommend that you stop by Liberty State Park. This park is not crowded and provides amazing spots for taking pictures of the classic New York Skyline without paying crazy ticket prices for the empire state building shot.

This park also features memorials for 9/11. I love this aspect of the park and how it pays tribute to those we lost that horrific day. The picture below is shot through one of the memories.

After you spent some time at the park, skip the ferry ride and drive into the city.

Transportation Costs in New York City 

Parking here can be a chore! I have found that the farther north you park, from Manhattan, the cheaper the rates are.

I have found parking for $20 a day in different locations with a mile or less walk to time square.

Uber is extremely expensive in the city and I highly suggest that you stick to walking and riding the subway or bus. This will typically cost you around $2.75 a ride or for a week of unlimited rides $32. (These prices are subject to change at any time)

Why do I not recommend uber, in New York City,  you may ask?

Well here is the story….after I rode the subway for 2 miles, got off and rode an uber for 1 mile for $35 (in the completely wrong direction, without knowing)….I walked an extra mile all for cheesecake. Haha now that I look back on this….I sound pretty desperate for some cheesecake. I was not happy paying $35 for just a mile….so I suggest that you ride the subway and walk.

Dessert heaven  

BUT!! This is not any cheesecake we are talking about here….this is Junior’s Cheesecake! I’ll let you in on this secret place….you gotta stop here for some dessert! It is amazing and worth the subway ride, $35 for the uber (in the wrong direction), and walking another mile for it.

I will say though, their regular menu food is not my favorite and I recommend eating dinner somewhere else and saving Junior’s for dessert. There are many local cheap eats along the streets around Junior’s.

Uber can be a great and affordable option though in other destinations.

New York City is so much fun to just walk around and see what you can stumble upon. We have stumbled upon people playing a grand piano in the streets to performing stunts with a huge crowd around cheering them on!

You never know what you will find for free by just walking around and being open to your surroundings.

My top things to do for free in New York City 

  • Central Park 
  • Time Square 
  • Walk the Brooklyn Bridge
  • China Town
  • Brooklyn Botanical Garden: typically there is a fee to explore the gardens, but you can get in for free on Tuesday and Saturday.
  • St. Patricks Cathedral.
  • Battery Park
  • Chelsea Market.
  • Grand Central Terminal 

2. Spend the night in Connecticut

After you have a full day in New York City, take the guesswork out of planning and make your way up the road to Hartford, Connecticut, for the night.

This has been our go-to stop along the route to the North! Why? Because the hotels here are super cheap and usually really nice….below you will find one, in particular, to stay away from.

In the morning you will love waking up to beautiful fall foliage. The parking lot, of our hotel, was gorgeous with the leaves resting so peacefully on the pavement…..it’s the small things in life right?

Now, this next step is up to you! You can either take the morning, half day, or full day to spend in Hartford or head on to Boston.

Unfortunately, we have not had the time to fully explore the city like we want to.

Where to stay away from 

We are including this stay on the blog because we are honest with you and want to warn you about things that are truly a bad experience. I would suggest staying away from the Knights Inn in Hartford….this may be a cheap option, but this place was too much for us! The room was ancient, the bathroom had leaks with buckets catching the water (so gross), and this was one of the dirtiest rooms we have ever stayed in. I typically read reviews before I stay somewhere….I must have missed this one…

I would opt for camping any day over staying there again.

Budget Hotels

There are many budget hotels in the area between $50-$80 a night. You will not have any problem finding a hotel here. Check out hotel rates by visiting the following link: Find top-rated hotels at the lowest prices.


3. Take almost a full day in New England’s Boston

You need just about a full day in Boston to get a small taste of the culture here. This is my favorite New England city!

The crisp cold air and the city streets provide a tranquil cityscape.

Where to begin your day in Boston 

Newberry Street

is a treelined, historical stone, and leisure outdoor shopping experience. I loved the couple of hours that we spent here. They have name brand stores and all types of specialty shops

. One of my favorites stores here was Frye. I love their shoes and the quality of them.

Shopping not for you or you got your feel in here?

Head over to Boston Public Garden for a relaxing time.

Talk about a writer and photographer’s paradise! This park had inspiration screaming from every corner.

Bridges, calming water, flowers, abundant trees, sculptures, benches, and grass calling my name. I could spend the whole day here no problem!

You can even take a ride on the swan boats during the summer.

After you have taken every picture possible and rested up pick any street and just start wandering around! We stopped in a random Italian bakery and found so many cool items imported from Italy and bread made fresh daily.

That is what I love about Boston, fresh food and the local businesses are abundant in this New England city.

Foodie Heaven in Boston 

My favorite restaurant in Boston is, of course, Neptune Oyster. This place has raving reviews and reservations are a must!! I highly recommend that you call a couple hours ahead of time to reserve a spot.

This place is always packed out and the main lobster roll here is to die for! One of the best meals I have ever had. This place was higher on my budget scale but this restaurant was worth it to me.

We typically eat out once during the day and stock up on grocery stories for healthy snacks and meals.

 Food options in Boston 

You can expect to pay $15-$20 for a middle of the budget restaurant within the city or you can opt for $5-$10 cheaper local spots for pizza or sandwiches.

Transportation in Boston 

Walk! This is very walkable. We walked during our time here, but if you’d rather save some energy, you can take the Subway (the “T”) for around $3.

Snack time 

ready for a snack or something refreshing to sip on? 

Boston Common Coffee Co. has delicious ice coffee and pastries! This place has some of the best coffee in New England (in my opinion). We enjoyed grabbing a coffee and following the Freedom Trail.

You can follow the Freedom Trail from the Boston Commons to the North End. You will discover some of the most famous historical sites along the way. Get your camera ready!

Done sipping on your refresher? Head over to the market right in downtown!

Downtown Market in Boston 

Here is where you can stock up on cheap, healthy snacks and meals for your road trip! The sellers are super friendly and love selling to fill your belly.

I can still smell the fresh fruits and veggies…

Where to stay in Boston 


The HI-Boston hostel is all about location, location, location. Close to Fenway Park and downtown, this cheaper option will have you smiling while saving a few bucks.

Budget Hotels

You can find budget hotels within an hour of Boston for $80 or less. Typically staying on the outskirts of the city will provide you with more budget-friendly options with breakfast. You can check out prices by going to the following link: Boston hotel rates.

4. New Hampshire for the day, Coast of Maine for the evening.

Pawtuckaway State Park will be your main destination in New Hampshire for this itinerary. quiet, peaceful, and stunning fall foliage, I was head over heels in love with this park. Don’t let the dirt roads scare you off, my husband’s old volvo made it just fine.

Experience fall on the water and release any stress from within.

Kayaking is amazing here and a perfect getaway from the noise of life.

Check out the park rentals if you are unable to bring your own equipment along.

Boat Rentals Per Hour Half Day Full Day Two Day
Tandem Kayaks, Canoes,& Paddleboards $20 $50 $85 $150
Single Kayaks $15 $50 $85 $150
Kids Kayaks $10 $50 $85 $150


There are plenty of hiking trails throughout the park and pets are allowed here!

Where to Stay


Camping within the park at one of the campgrounds will have you at around $23 for no hookups all the way up to $50 with hookups. Cabins are also available and range from $65 to $80 for a night.

Budget Hotels

Or you can venture to Rhode Island for the night and pick a local hotel with cheap rates! They are in abundance here, so you should not have any problem finding a place to fit your budget.

5. Rhode Island and heading home

Where to go 

Your last stop of the trip, Rhode Island. You will spend your morning here and start making your way back home after lunch.

Take a drive along the coast and check out the coastal shops! We enjoyed our walk along the boardwalk here.

Watch Hill Yacht Club, Westerly Rhode Island 

Make sure to grab some gelato at one of the shops here before you start heading back home!

We had a 9-hour journey back home, so we did stock up on some snacks here before knocking down some mileage for home.

Final Tips on New England Travel

  • Make sure if you are booking a hotel they have breakfast
  • Make sure to have some dollar bills and spare change. There are tolls up North
  • Stock up on snacks and other smaller meals at the grocery store
  • Use the Gas Buddy app to find the cheapest gas
  • Take tons of pictures and make some memories
  • Find cheap car rentals by checking out Skyscanner.


Not sure what to pack for your New England adventure? Check out our blog on Affordable Travel Gear.



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