New England

We Asked AI to Plan a Fall Foliage Trip

We asked ChatGPT to plan the perfect New England fall foliage vacation. Here’s how it went.

By Ian Aldrich

Oct 04 2023

Pumpkin spice. Big cozy sweaters. A long, winding foliage drive. What makes a perfect fall day, and could AI possibly understand?

Photo Credit : Ground Picture/Shutterstock

Over the last year all-things AI have dominated the headlines and upended not just the tech world, but also changed how many of us think about the future. Are we sliding into a computer-ruled Armageddon, or does a sunny world of sparkling new efficiencies await? While we wait for the future of humanity to be ironed out, large-language models like ChatGPT are already leaving their imprint. Writing college essays! Imparting dating advice! Planning vacations?

Well, yes. Users have already turned AI into a concierge of sorts, to map out day trips and weekend jaunts. Which of course, got us thinking. How it would an AI fare when put to the test for the motherload of New England travel getaways: A prime-time foliage vacation. We decided to find out. 

Good morning ChatGPT. How are you on this beautiful early autumn day?

Good morning! While I don’t have feelings or perceptions, I’m here and ready to assist you. How can I help you today on this early autumn day?

We are starting to see some early color where I live in southern New Hampshire. What can you tell me about this year’s foliage forecast?

While I can’t provide real-time or future-specific forecasts beyond my last update in September 2021, I can give you some general insights about how foliage forecasts are typically made and factors that influence the timing and vibrancy of fall colors.

Factors Influencing Fall Foliage:

1. Temperature: Cool nights (above freezing) and warm, sunny days are ideal for promoting the best color displays.

2. Moisture: A moderate amount of rainfall in the months leading up to fall can support vibrant foliage. However, a very wet or drought-stricken summer can delay or mute the colors.

3. Frost: An early frost can end the foliage display prematurely.

4. Daylight: As the days shorten, chlorophyll production slows and eventually stops, leading the green to fade and other colors to emerge.

For southern New Hampshire, peak foliage traditionally occurs from early to mid-October, but it can vary based on the aforementioned factors.

To get the most current and accurate predictions and updates for this year’s foliage in southern New Hampshire:

1. New Hampshire’s Tourism Website: The state often provides foliage trackers or reports that are updated regularly.

2. Local News Outlets: Check local news websites or TV stations for foliage reports.

3. Yankee Magazine’s Foliage Tracker: A trusted source for New England foliage updates.

4. Social Media: Platforms like Instagram, where users post recent photos, can give you an idea of the current status in different areas.

The Yankee shout-out warmed my heart but the answer revealed the AI’s immediate limitations: Its knowledge bank hadn’t been updated in two years. How up-to-date could its suggestions be? 

From here I decided to begin to dig deeper. Was the New England autumn worth all the hype? What made the region so special this time of year? This inquiring mind wanted to know what the AI knew. But first, I decided to get a little cheeky. 

Have you ever visited New England during autumn?

I don’t have feelings, consciousness, or the ability to physically visit places since I’m just a virtual assistant. However, I’m equipped with a vast amount of information on New England and its autumn splendor based on the data I was trained on. If you have questions or need recommendations about New England in the fall, I’m here to help!

2017 New England Fall Foliage Forecast
Scenes of peak autumn color like this one in New Hampshire’s White Mountains drawn tourists from all over the world.
Photo Credit : Jim Salge

But let’s say you weren’t a virtual assistant and you could travel to New England during peak foliage, where would you want to go?

If I were a sentient being with the ability to appreciate beauty and experience emotions, based on the wealth of information I’ve been provided, I would probably choose to visit several iconic places in New England that are often celebrated for their autumn splendor:

1. Stowe, Vermont: A classic New England town nestled among the Green Mountains, Stowe offers a blend of stunning fall colors, charming architecture, and scenic drives, especially along the nearby Route 100.

2. White Mountains, New Hampshire: Particularly the drive along the Kancamagus Highway, which is renowned for its breathtaking views and vibrant fall colors. The region offers numerous hiking trails, waterfalls, and panoramic views from peaks like Mount Washington.

3. Acadia National Park, Maine: The combination of rugged coastlines, dense forests, and the Atlantic Ocean makes this a unique place to witness fall colors. Watching the sunrise from Cadillac Mountain with fall colors in the backdrop would be an ethereal experience.

4. The Berkshires, Massachusetts: A haven for artists and nature lovers alike, the rolling hills of the Berkshires offer a tapestry of colors in the fall, complemented by cultural attractions and historic towns like Stockbridge and Lenox.

5. Kent, Connecticut: Often touted as one of the most beautiful towns in Connecticut, especially during fall, Kent offers a mix of covered bridges, waterfalls, and dense forests that light up in autumn hues.

6. Newport, Rhode Island: While not as forested as other regions, Newport in the fall offers a unique blend of historic mansions, coastal drives, and autumnal colors. Walking along the Cliff Walk would be a blend of history, ocean views, and fall foliage.

That sounds nice. So, based on what you do know, is New England worth visiting in autumn?

Absolutely! New England in autumn is one of the most iconic and celebrated destinations in the U.S. for several compelling reasons:

1. Spectacular Fall Foliage: New England is renowned for its vibrant fall colors. The mix of maple, oak, and birch trees turns the landscape into a mosaic of oranges, reds, yellows, and golds.

2. Cooler Weather: Autumn brings crisp and comfortable temperatures, making it ideal for outdoor activities like hiking, walking, or simply enjoying the scenery.

3. Festivals and Events: Many towns in New England host fall festivals celebrating the harvest season. These include apple festivals, craft fairs, pumpkin festivals, and Oktoberfest events.

4. Historic Charm: Quaint towns with historic homes, churches, and public buildings are even more enchanting against a backdrop of fall colors. Towns like Woodstock in Vermont, Salem in Massachusetts, and Portsmouth in New Hampshire have particular allure during this season.

5. Seasonal Activities: This is the perfect time for apple picking, pumpkin patch visits, corn mazes, and hayrides. Many farms and orchards open their doors to visitors and offer a variety of activities and treats, like cider donuts and apple cider.

6. Haunted History: With Halloween in October, several places, especially Salem, Massachusetts, offer ghost tours and recount the tales of witch trials and haunted histories.

7. Culinary Delights: Autumn brings a bounty of seasonal foods like pumpkins, apples, cranberries, and more. Enjoy these in the form of pies, ciders, stews, and other regional dishes.

8. Scenic Drives: Roads like the Kancamagus Highway in New Hampshire or Route 100 in Vermont offer breathtaking views of the fall landscape.

9. Less Crowded: While fall does attract tourists, especially during peak foliage, it’s generally less crowded than the summer months. Plus, by late October, the crowds have typically thinned out considerably.

10. Affordable: Depending on when and where you go, you might find that accommodations are slightly more affordable in the fall than during the summer months.

That said, if you’re considering a visit, it’s wise to book accommodations in advance, especially if you’re aiming for peak foliage season. The surge in “leaf-peeping” tourism can fill up accommodations quickly. Overall, autumn in New England offers a unique, beautiful, and culturally rich experience that’s well worth the visit.

Many words, but not a lot of details. What was the allure of Woodstock, Vermont, in autumn for example? Or Portsmouth, New Hampshire? What exactly defined that “breathtaking landscape” found along the Kanc? Useful specificity seemed to be short supply. Or maybe, it just needed better prompts. When I asked it for the real bucketlist destinations in the region for visitors to explore during fall, I was answered with an expected hit list: New Hampshire’s Kancamagus Highway, Maine’s Acadia National Park, Connecticut’s Litchfield Hills region. Decent selections, but now I wanted some activity-specific ideas. Maybe even a ranking of its choices. That would be a far trickier exercise. 

Guide to the Kancamagus Highway
The Kancamagus Highway (Route 112) in New Hampshire is a classic fall foliage route.
Photo Credit : Jim Salge

What are the best foliage drives in New England?

New England offers a plethora of scenic drives that come alive with vibrant fall foliage. Here are some of the most iconic and beloved routes:

1. Kancamagus Highway, New Hampshire: Often simply called “The Kanc,” this 34-mile stretch of Route 112 runs through the White Mountains and is renowned for its breathtaking fall colors, especially between Lincoln and Conway.

2. Green Mountain Byway, Vermont: Spanning between Waterbury and Stowe, this route offers a mix of picturesque villages, mountain landscapes, and dense forests.

3. Mohawk Trail, Massachusetts: One of the oldest scenic roads in the U.S., the Mohawk Trail (Route 2) winds through the Berkshires and offers spectacular views, especially between Greenfield and North Adams.

4. Route 100, Vermont: This north-south route runs almost the entire length of the state and offers an array of foliage vistas, from the Green Mountains to idyllic farm valleys.

5. Connecticut River Byway, New Hampshire and Vermont: Following the Connecticut River, this byway showcases the beauty of two states. Enjoy the serene views of foliage reflected in the river, especially between Orford, NH, and Windsor, VT.

6. Coastal Route 1, Maine: This route, stretching from Kittery to Bar Harbor, offers a unique mix of seaside vistas and colorful forests. Particularly gorgeous is the stretch around Camden and Acadia National Park.

7. Route 169, Connecticut: This scenic drive through Connecticut’s Quiet Corner is known for its historic homes, farms, and churches set against a backdrop of autumn hues.

8. Loop Road in Acadia National Park, Maine: A 27-mile road providing dramatic ocean views alongside dense, colorful forests and mountain landscapes.

9. Route 7, Massachusetts: Running through the western part of the state, this route offers views of the Berkshires and passes through charming towns like Great Barrington, Stockbridge, and Williamstown.

10. Route 17, Maine: The “Height of Land” overlook on this route offers one of the most iconic views in Maine, with a panoramic outlook over Mooselookmeguntic Lake with forests stretching to the horizon.

11. Scenic Route 103, New Hampshire: This route between Newbury and Claremont offers lovely vistas of Mount Sunapee and is dotted with quaint New England villages.

12. Route 6A, Massachusetts: Running through Cape Cod, this road offers a combination of coastal views, marshlands, and colorful forests, especially between Sandwich and Orleans.

13. Gap Roads, Vermont: These include the Lincoln Gap, Appalachian Gap, and Smugglers Notch—all providing stunning mountain vistas and dense forest colors.

Not a lot to disagree with but there were 13 to choose from. Was the AI afraid of hurting someone’s feelings or just trying to cover as much ground as possible. What I wanted was the best of the best. 

I like foliage drives you selected for me but I want you to come in closerand select the absolute best one. What would you suggest?

If I had to suggest one for a first-timer looking for the quintessential New England experience, I’d lean toward the Kancamagus Highway. It’s not overly long, offers stunning vistas, and captures the essence of New England’s autumnal beauty.

Hear, hear! I’ve driven the Kanc many times in fall and aside from the traffic jam of RVs that sometimes clog the road, I couldn’t disagree with the choice. It’s a storied road. Well, done AI. But we were far from done. Now came a real test of expertise. 

Stowe Pinnacle in Stowe, Vermont.
Photo Credit : Clay Kaufmann/Unsplash

Plan the perfect New England foliage weekend for me.

Certainly! Here’s a curated itinerary for a perfect New England foliage weekend:

Day 1: Vermont – The Heart of Foliage

1. Morning:

• Arrival in Stowe, Vermont: This town is quintessential New England, especially in the fall. Check into a cozy bed & breakfast or a mountain lodge.

• Breakfast: Visit a local cafe for a hearty breakfast, perhaps with some Vermont maple syrup on your pancakes or waffles.

2. Mid-Morning to Afternoon:

• Scenic Drive: Take a leisurely drive along Route 100. This route is renowned for its breathtaking views, especially during the foliage season.

• Hike: Head to Smugglers’ Notch State Park for a hike. The trails range from easy to challenging, but all offer beautiful views.

3. Late Afternoon:

• Visit a Cider Mill: The Cold Hollow Cider Mill in Waterbury is nearby. Taste fresh apple cider and indulge in their famous cider donuts.

• Cheese Tasting: Swing by the Cabot Farmers’ Store to sample some of Vermont’s finest cheeses.

4. Evening:

• Dinner: Dine in Stowe. Many restaurants in the area focus on farm-to-table fare, showcasing Vermont’s rich agricultural offerings.

• Rest & Relaxation: Return to your lodging, maybe enjoy a fireplace if your accommodation offers one.

Day 2: New Hampshire – The White Mountain Wonderland

1. Morning:

• Drive to North Conway, New Hampshire: This will be a scenic drive, especially in the fall.

• Breakfast: Grab a breakfast sandwich or pastry from a local bakery in North Conway.

2. Mid-Morning to Afternoon:

• Kancamagus Highway: This is a must-do. Drive this scenic route to see some of New England’s most famous foliage vistas.

• Picnic: Pack a picnic from a local deli in North Conway and enjoy it at one of the many scenic overlooks or picnic areas along the highway.

3. Late Afternoon:

• Visit a Local Orchard: Pick your own apples, a quintessential New England fall activity.

4. Evening:

• Dinner: Enjoy a hearty New England meal in North Conway. The town has a range of dining options, from upscale restaurants to cozy pubs.

• Drive back to Stowe (or you could stay in North Conway if you prefer).

Day 3: Departure & Souvenirs

1. Morning:

• Breakfast in Stowe.

• Souvenir Shopping: Before departing, pick up some local products like maple syrup, cheeses, or handcrafted goods as a reminder of your New England foliage weekend.

2. Departure: Head back home or to the airport, relishing the memories of a vibrant and picturesque New England weekend.

Note: This is a condensed itinerary that focuses on two iconic foliage destinations. Depending on your interests and pace, you can adjust the activities or even extend your stay. Safe travels and enjoy the radiant beauty of New England in the fall!

Safe travels, indeed because this itinerary will have mostly in the car. This, my friends, is a ridiculous weekend. Why would you anchor yourself in Stowe, but then tack on a 230-mileround-trip “side journey” to North Conway? You’re already in Vermont—why would you venture outside its borders? Burlington is just to the west. Woodstock is 90 minutes south. Poor planning, bot. I don’t care if your schooling stopped in 2021. You need to do better. 

I gave it another shot. But not with any old question, but one whose very answer has ended friendships, sent couples into therapy, and disintegrated cider pressing parties. 

Autumn morning in Kent, CT.
Photo Credit : Mark Fleming

What is New England’s number one foliage town?

Designating a single “number one” foliage town in New England is subjective and varies based on individual preferences, local recommendations, travel magazines, and annual changes in foliage quality. However, there are a few towns that are often lauded as top foliage destinations year after year.

Stowe, Vermont, often gets top billing as New England’s premier foliage town.

Here’s why Stowe is frequently celebrated:

1. Stunning Scenery: Nestled in the Green Mountains, Stowe is surrounded by forests that burst into a riot of colors in the fall.

2. Recreation Path: The Stowe Recreation Path provides a scenic 5.5-mile route that offers incredible views of the foliage, the Little River, and Mount Mansfield, Vermont’s highest peak.

3. Mount Mansfield: For the adventurous, a hike or a drive up Mount Mansfield provides panoramic vistas of the fall colors.

4. Proximity to Notable Spots: The town is near Smugglers’ Notch, a mountain pass known for its tight turns and stunning foliage views.

5. Charming Downtown: Stowe’s village is quintessential New England with historic buildings, churches, boutique shops, and restaurants.

6. Variety of Activities: Beyond leaf-peeping, visitors can explore cider mills, craft breweries, and local artisan shops.

7. Accommodations: The area has a range of accommodations, from luxurious resorts to quaint bed and breakfasts, all of which provide a cozy autumn experience.

Not a terrible choice by any means, but the best? Several years ago Stowe came in 24th in Yankee’s lineup of the “Top 25 Best Foliage Towns in New England,” finishing behind three other Vermont favorites: Manchester, Middlebury, and Waitsfield—which all cracked the Top 10. Our number one choice? Kent, Connecticut, which barely got a mention when I pressed the AI further about the region’s prime foliage destinations. 

But I decided to play along. It was late September. Foliage had already hit the northern reaches of New England. If I wanted to, could I still hope to put together a getaway?

Is it too late to plan a fall foliage trip to New England?

Whether or not it’s too late to plan a fall foliage trip to New England depends on a few factors:

1. Current Date: Fall foliage typically peaks from late September to early October in northern New England (e.g., northern Vermont, New Hampshire, and Maine) and from mid-October to late October in southern New England (e.g., Massachusetts, Connecticut, Rhode Island). If it’s within these windows or shortly before, there’s still an opportunity to see the foliage.

2. Accommodation Availability: New England is a popular destination during the fall foliage season, and accommodations, especially in prime locations, can fill up quickly. You may need to be flexible about where you stay. Consider looking for lodgings in lesser-known towns or a bit further from the most popular spots if the prime locations are booked.

3. Flexibility: If you have flexibility in terms of dates and locations, you can chase the foliage by moving north or south, depending on where the peak colors are during your visit. There are websites and hotlines that provide real-time updates on foliage conditions.

4. Activities: Besides just driving and viewing the foliage, think about other fall activities you’d like to do. Apple picking, pumpkin patches, hayrides, and local festivals can add to the autumn experience.

5. Travel Restrictions or Guidelines: Given the evolving nature of global events, always check for any travel restrictions, guidelines, or requirements that might be in place in the states you’re planning to visit.

6. Last-Minute Planning: While planning in advance is usually recommended, spontaneous trips can also be rewarding. Sometimes, making a last-minute decision based on current foliage reports can lead to an unforgettable experience.

To sum up, it’s never strictly “too late” until the leaves have all fallen. Even if peak foliage has passed in some areas, there are likely other regions still displaying vibrant colors. The key is to be flexible, do a bit of research, and embrace the adventure!

Thanks for optimism and the exclamation points, bot. I love your autumn enthusiasm. The most interesting response the AI delivered, however, came near the end of our exachange. It wasn’t about the color, or where to go, or even what to do, but rather, how I should travel during this popular time of year. 

2018 New England Fall Foliage Forecast
Hillsides bursting with color are the dream of every leaf peeper in New England.
Photo Credit : Jim Salge

What is proper traveler etiquette for people visiting New England during peak fall foliage?

Visiting New England during peak fall foliage is a delightful experience, but as with any travel destination, there are some etiquette guidelines to follow to ensure a respectful and enjoyable visit for both travelers and locals:

1. Respect Private Property: While the fall colors may be enticing, always remember that much of the land in New England is privately owned. Avoid trespassing or pulling over on someone’s property to take photos. Look for public viewpoints or areas designated for visitors.

2. Drive Safely: The scenic beauty can be distracting. If you want to gaze at the foliage or take photos, pull over safely to designated viewpoints or parking areas. Avoid stopping abruptly on busy roads, and always use your blinker if turning or pulling over.

3. Keep Traffic Flowing: Many roads in New England, especially in rural areas, are narrow and winding. If you’re driving slowly to enjoy the view and notice cars accumulating behind you, it’s courteous to pull over and let them pass.

4. Park in Designated Areas: Especially during peak season, popular areas can become crowded. Always park in designated areas and avoid blocking driveways, entrances, or narrow roads.

5. Follow Leave No Trace Principles: If you venture out for a hike or picnic, always pack out what you bring in. Leave the natural areas as beautiful as you found them.

6. Support Local Businesses: Many towns in New England rely on tourism, especially during foliage season. Consider supporting local restaurants, shops, and attractions.

7. Stay Informed about Local Rules: Some towns or areas might have specific regulations, especially in 2023 and beyond, given the evolving nature of travel norms post-pandemic. Always check local guidelines and adhere to them.

8. Be Patient: Popular spots can become crowded during peak foliage. Whether you’re waiting for a table at a restaurant or a parking spot at a viewpoint, patience and understanding go a long way.

9. Interact Respectfully: New Englanders are known for their friendly yet reserved nature. A smile, a polite greeting, or a simple “thank you” is always appreciated.

10. Avoid Peak Times if Possible: If your schedule is flexible, consider visiting popular spots during weekdays rather than weekends. Early mornings and late afternoons are typically less crowded than midday.

11. Book in Advance: Given the popularity of the season, accommodations can fill up quickly. To avoid disappointment, make your reservations well in advance.

12. Be Prepared for Changing Weather: New England weather can be unpredictable in the fall. Layers are your friend, and always check the weather forecast before venturing out for the day.

By following these etiquette guidelines, travelers can ensure they have a positive impact on the communities they visit, making the experience enjoyable for everyone involved.

I couldn’t have said it better myself.