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 RoadTrippers.com 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 RoadTrippers.com. 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 AngieAway.com 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 www.Enterprise.com.

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