Planning the Perfect Fall Road Trip

Welcome to Florida in October. It’s 90 degrees and I just got back from the pool.

I’m not complaining – it’s a lovely life down here in the Sunshine State – but I confess, having lived in New York City for 5 years, October is the beginning of several months of longing for the City that Never Sleeps. I miss dramatically changing leaves and brisk, but still comfy, temperatures, and the slide into the twinkling holiday season. Plus, there’s a neglected section of my closet with boots, scarves and cute coats that remains untouched for 10 months a year now that Angie Away Base Camp is in Florida full-time.

Planning a Fall Road Trip with Enterprise

I really really really love Autumn in New York

When Enterprise Rent-a-Car asked me to dream up an ideal fall road trip, my mind immediately went north – straight to colorful leaves, roaring fireplaces, apple cider and me wearing leg warmers and an infinity scarf without some flip-flip & tank-top clad surfer giving me the stink eye. As soon as we dip below 80 degrees, you can bet I’m wearing boots.

Planning a Fall Road Trip with Enterprise

Central Park in NYC

But back to planning that fall road trip. I never quite understood their appeal until our #OrthAmerica road trip last year, when my brother, sister and I drove from Denver to Seattle. The wide open spaces of Colorado, Wyoming and Idaho wowed us around every bend in the road, and I was surprised at just how easy it was to plan and how relaxing the driving aspect of the trip seemed to be. Normally if I’m in the car for 5 hours, it’s because I’m trying to get from Point A to Point B in a hurry. But our #OrthAmerica road trip was about the journey, and it made me a fan of the unrushed, open-to-adventure style road trip.

Planning a Fall Road Trip with Enterprise

Road tripping with the Orth siblings

Fall is an ideal time to plan a road trip because in most places its considered shoulder season. The summer crowds are long gone, temperatures are cozy and hotels are less expensive than they are during the peak holiday months.

Having tested out some road trip theory out west, here’s my manifesto!

Angie Away’s Rules of the Road Trip

1. Choose a quality co-pilot. I love solo travel when I’m jaunting across the world on assignment, but road trips are much better with a fun companion. Last year I had my brother and sister along for the ride and it was hands-down one of our top sibling memory-making experiences. For the Maine-Florida trip, I’d take Rick, who’ll be my bonafide lifetime copilot by then. Yay for newlywed adventures!

2. Prioritize local & seasonal food. Hangry Angie is not a good person, so we’ll be prioritizing food above just about everything else on our first married road trip. I want to eat the best of the best in each place we visit, so there will be no truck stops or fast food for us. Just local & seasonal deliciousness.

3. Mix up the itinerary. I used to plan our quirky Western road trip, and was really pleased at how much we saw off the beaten path. You can even click the Fall Foliage option and it’ll tell you the best places to leaf peep – how convenient is that?! We’ll definitely use this resource for our fall road trip.

4. Decide how far you want to drive & book accommodations in advance. The only thing I really planned ahead on our last road trip was accommodations. It gave us a driving goal each day – anywhere from 3-6 hours throughout the day was easy to manage, and it gave us lots of time for unscheduled exploring, meeting interesting people and eating. (See No. 2)

5. Upgrade your vehicle. Rental car prices can be as low as $9.99 a day, so there’s really no reason to put mileage and wear and tear on your own vehicle. Plus, you can upgrade to something fancier/sportier/roomier than your usual ride, which is a nice little boost of fun for the trip.

Though wedding planning has absolutely taken over my life like a flesh-eating virus, in between meltdowns, heaving sobs and punching inanimate objects, I’ve already begun mapping out our first fall road trip as husband and wife – a top to bottom tour of the East Coast.

Here are my major fall road trip photo goals: 

  1. Baby farm animal
  2. Pumpkin patch
  3. Flannel
  4. Apple-picking
  5. Hay ride
  6. Corn maze
  7. Red, yellow & orange leaves
  8. A dilapidated barn
  9. Photo holding apple cider or a PSL and looking cold

*Bonus points awarded for combining these elements in to one photo.

If we drive 5 hours a day, our itinerary should take 4 days & about 1,300 miles or so, but there’s so much to see, I might try to stretch it even longer. To start, we’ll rent a car at a local Enterprise location in Maine, bundle up in some adorably cliché flannel ensembles and wake up early to see the first glimpse of sunrise in the United States. Cadillac Mountain in Bar Harbor offers panoramic views and seems like a great spot to start the adventure. Up next, we’ll check out the Fryeburg Fair and consider taking home an adorable baby goat… naaaaaah, we’ll stick with homemade canned goods. If I can fit in at least 3 square meals where lobster is the Maine (get it?) ingredient, I’ll consider our trip off to a successful start.

Planning a Fall Road Trip with Enterprise

Suggested route from You can customize to include all sorts of interesting stops – historic sites, natural features and changing leaves!

In about 200 miles we’ll end up in Massachusetts where I’ll subject Rick to apple-picking on some picturesque family farm. We will blow up Instagram with our flannelly newlywed love. (The outtakes will be on Snapchat, obviously.  Follow along! -AngieAway)

I’m excited to take the Cross Sound ferry from New London, Conn., to Orient Point on Long Island.  Rick’s family is scattered all around the Hamptons area, so we’ll have fun time catching up with everyone, dragging them to some photogenic pumpkin patch, and then exploring some of the famous wineries in the area. (All those years I spent in NYC and never once ventured out to Long Island! Shame on me!)

After we get the requisite perfect fall Instagrams out of the way, the next several hundred miles will be food-focused and filled with Philly cheesesteaks, Maryland blue crab, Virginia ham, North Carolina barbecue and South Carolina shrimp & grits. We’ll search out corn mazes, hay rides and the old barn as we venture further south, hoping to burn off the calories…

Our final stop before we make a beeline for home will be gorgeous Savannah. Depending on our schedule, we might be lucky enough to catch the Tybee Island Pirate Fest before leaving our flannel & boots at the Florida-Georgia state line when we inevitably will begin to sweat.

It’s back to Autumn in Florida, after all.

Planning a Fall Road Trip with Enterprise

I just wanna wear a scarf.

Thanks to Enterprise Rent-a-Car, I’ve got $100 gift card to give away to one lucky reader. I suggest using it on your fall road trip, but you can also spend it on pumpkin spice lattes & flannels to make all your autumnal Instagram dreams come true.

All you have to do to enter is leave a comment below telling me who you’d take on your ideal fall road trip and where you’d go. Pretty easy, right? I’ll randomly choose a winner on Nov. 6, 2015.  Nov. 9, 2015 UPDATE — Congrats to reader Nichole on winning the $100 gift card from Enterprise. Keep an eye on for lots more giveaways to come!

Be the first to hear about giveaways! Sign up for the Angie Away Newsletter here!

This post was made possible by Enterprise Rent-A-Car. Road trip tips & cliche photo suggestions are my own. For more information about Enterprise and to rent a car for a future road trip, visit

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53 thoughts on “Planning the Perfect Fall Road Trip”

  1. Mid-October till New Years is when I miss New York the most as well. My roommates and I took two fall road trips while I was living there, up to Litchfield, CT and the Hudson River Valley. (I never made it out to Long Island either, oops.) I’d love to do the Finger Lakes and Niagara Falls one Autumn, and drag along as many of my cousins as I could convince to go!

    You road trip sounds great, especially the planned food stops – have fun!

  2. Fall in Washington DC is my favorite time of year – but I’d love to snag that gift card and head up 95 to New England. I’ve only done NYC and Boston — would love to explore the treasures of Rhode Island, Maine, Vermont and New Hampshire too!

  3. Michelle Craven

    I would take my husband and daughter on a road trip through the great Southwest. Grand Canyon, Sedona, Zion NP, Bryce Canyon, and Las Vegas. We all think that would be a blast!

  4. Definitely would explore va to enjoy the beautiful fall colors! Always love how UVA looks in the fall, and Shenandoah national park is amazing. I’d love to explore the little mountain towns to see what they have to offer

  5. I would take my friend Christine up from NY to Rockport, Maine! She’s never been to Maine and it’s one of my favorite road trip destinations from here. To see that drive in the fall is bliss.

  6. I’d take my Boyfriend. The fall is like “our” season. We usually head up to Lake Placid, NY for a trip, but I’d love to go to Montreal with him or New Hampshire, as he talks about it all the time and I’ve yet to visit. We are travel partners in crime! 🙂

  7. I would love to do a road trip to through the northeastern region of the U.S.A., starting in Chicago and ended up over near Maine. I would bring along my three best friends and make it into a fun ladies road trip!

  8. Perfect fall roadtrip? Finally hitting all the western National Parks that are too crowded in the summer! I can’t deal with crowds, so I’ll be avoiding New England this time of year 🙂

  9. I haven’t seen my best friend since travelling NZ this spring and we’ve always talked about our perfect road trip between our two homes – Philadelphia (Me) and Indianapolis (Her) but we’d probably go way out of way to get there!

  10. I’d invite my parents to join me in bee-lining out of Florida up to the Northeastern states to see autumn’s splendor!

  11. I would definitely use it on our east coast road trip, which I’m in the middle of planning. I can’t wait to read all about yours because I’m having a really hard time narrowing down everything I want to do. At this point, it’s going to take about 4 years to do all that I want 😉

  12. I’d take my roommate Abby and we’d roadtrip from Salt Lake City down to the Grand Canyon because neither of us has been before!

  13. I have dreamed of a fall road trip up in the NE, especially Maine! I would most defiantly take my husband and we would consume as much seafood as our bodies would allow. We don’t really have maples here so seeing all the amazing colors of the fall in the NE would be a dream come true.

  14. candace normoyle

    I would def take my kiddos either north to burlington vt which is beautiful this time of year or go south to fl to get warm!!!

  15. I would take my wonderful husband, Matthew, and I want to go to Niagra Falls!! I’m obsessed with seeing it before i die! An ultimate bucket list trip!

  16. I would road trip with my son Logan and my grandma to Tennessee to see the beautiful colors of fall and do some hiking! I love a good road trip!!

  17. The hubs and I would head north from Savannah and head to Harper’s Ferry, WV. It’s beautiful year-round, but especially in the Fall.

  18. Hi Angie!
    I absolutely love road trips and would naturally bring my boyfriend, Jamie 🙂 One road trip I’d like to do is out in Arizona/Southern Utah. I would love to see Sedona, Havasu Falls, and Bryce Canyon… especially during fall because it’s the perfect time to go! Not extremely hot, not extremely cold… but very comfortable! 🙂
    BUT …. any road trip in fall sounds fabulous.. I NEED A BREAK!

  19. I would leave the husband and kids at home and take my best friend on a road trip to some place neither of us have been. We’ve both lived in California but never visited a redwood forest. I think that would be a definite stop on our trip.

  20. I would totally go to our farm in North Florida. It’s fall up there for my kids. They have grown up in Florida and even the cooler weather and campfire make them know it’s fall in Florida! And of course I’d take the whole family!

  21. I would take my best friend Shauna to the Grand Canyon then up through California!

    Side note, my parents have a beautiful house in Conway, New Hampshire, so if/when you do this road trip you’ve got a free place to stay with some fun locals 🙂

  22. I would love to hit the road to New England with my husband! From Chicago, we’d stop by Niagara Falls, visit our friend in Vermont, and then head down a little ways to Boston.

  23. I would go on another U.S. National Park road trip with my partner in crime (and blogging), Rachel! We have already done a long road trip to TWELVE different national parks on the west coast but it’d be wonderful to have the chance to explore the many gorgeous east coast parks.

  24. Autumn road trips are the best! I live in Montana but grew up in Vermont, so New England is what I think of what this time of year rolls around. I road tripped out here to Missoula MT when I was 19 yrs old and I’ve been dreaming of retracing my route back home, now 15 years later. My co-pilot would most definitely be my sweet and adventurous dog, Mazzy!

  25. I would take my grandma on a road trip up the entire west coast. She hasn’t gotten to travel too much being a young mom then caring for my grandfather whom passed of cancer. She deserves some fun!

    1. You’ve won the gift card, Nichole! Send me an email – angieawaymedia at gmail dot com by Nov. 13 to claim your prize. Congrats! Hope you have a blast with your grandma!

  26. I would road trip with my husband and kids. I’m one of those freaky people that don’t mind traveling with kids…it just has to be planned right. We would travel north stopping in D.C. And heading straight to New York.

  27. I’d take my husband, who has just been declared in remission from gallbladder cancer, on a coastal historical road trip starting in Boston, then NYC, hit Philadelphia, down to DC, Williamsburg and Jamestown are a must, and then we’d make our way down to St Augustine. I’m sure there are other stops along the way which elude me at the moment!

  28. I would take my 15 yr. Old daughter..ROADTRIP!!!!! She’s never been north of the mason dixon line….we would have a blast.

  29. Hi Angie! I would take my beautiful mother with me and we would set out on a an adventure with several different goals:
    -The first would be to eat our way through – so we would pinpoint the very best candy apple spots, fresh seafood, old time candy stores, farmers markets and fall festivals. I’d make sure to have her take embarrassing selfies with mouths full of food. – Helen, Ga comes to mind, as does Cosby, Tenn, Asheville, NC . We’d undoubtedly have to throw a BBQ stop in there somewhere. My mom always says to have a “good mix of salty and sweet – if you can’t get the balance, you just have to keep eating more of each.” 🙂
    -The second would be to seek out all of the cute tiny houses that are popping up through out the country. That’d take a little research but there is a pop-up gypsy carriage tiny house sitting somewhere here on the east coast. We’d add in some tree house stops too of course.
    -Then lastly, we’d make sure we were pulling as many pranks as possible…my mom is 60+ now so I figure she should be able to start getting away with things…think Bad Grandpa…can’t wait til I’m in that age range.
    That’s just a little bit about the way we’d be working our way up the east coast and into the smokey mountains! Thank you for all of the great tips, and now I’m just itching to get on the road!!

  30. I’d love to road trip through the Washington and Oregon apple country! I’m from western New York and grew up in the heart of apple country. I actually lived in the middle of an apple orchard during my teen years and would grab an apple off the tree on the way to school in the morning. I’d love to experience that in another region known for it’s orchards and stunning scenery. Here in Denver, I miss picking fresh berries from the vine, apple cider, and real fall color (Don’t get me wrong, the Aspens are beautiful in the fall! — But I miss those reds and oranges as well!)

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