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The Maine Chick and The ExploreHer’s Guide to Fall in New England

Updated: Aug 24, 2023

Your Guide to Making the Most of Fall in New England Begins Here.

It’s officially fall, y’all! Autumn is, without a doubt, one of the best seasons to visit New England. The vibrant, colorful foliage sweeping across the northeast this time of year turns the region into one of the top leaf-peeping destinations in the entire country. From taking scenic drives down long, enchanting roads to hiking up red, orange, and yellow mountaintops to picking fresh apples and pumpkins to sucking down pumpkin spice lattes and devouring apple cider donuts, there are endless ways to make the most of fall in New England.

As Maine natives, The Maine Chick and The ExploreHer have spent years making the most of fall in The Pine Tree State. Our love of autumn has also inspired us to discover ways to make the most of fall in nearby New England states!

Whether you’re a New England native looking for new ways to enjoy fall this year or a tourist planning a fall-themed trip to the northeast, our favorite things to do, places to see, and products to enjoy in the fall are sure to inspire you this season. Explore our fall guide to make the most of this special time of year!

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While a classic scenic drive might be a great way to admire the foliage, why not experience the fall colors up close and personal? Here are a few of our favorite hikes (ranging from easy to difficult) to take in the foliage across three New England states: Maine, New Hampshire, and Vermont.


Bradbury Mountain State Park - The Maine Chick’s Pick

Bradbury Mountain State Park is located in the town of Pownal, Maine. The park's 800 acres offer trails perfect for hiking, biking, and equestrian activities. Although Bradbury Mountain has little elevation gain, the summit offers a great foliage view!

  • Location: Pownal, Maine (near Freeport)

  • Difficulty: Northern Loop Trail (easy) and Boundary Trail (easy/intermediate)

  • Distance: 1.4-mile loop for the Northern Loop Trail and 2.2-mile loop for the Boundary Trail

  • Elevation: 485 ft

  • Estimated time: On average, it takes 37 minutes to complete the Northern Loop Trail and 57 minutes to complete the Boundary Trail

  • Estimated price: Bradbury Mountain charges a daily use fee, $4.00 for an Adult Maine Resident and $6.00 for a Non-State Resident



Jordan Pond in Acadia National Park - The ExploreHer’s Pick

Located off the two-way section of Park Loop Road, Jordan Pond is an iconic area of Acadia offering outstanding views for canoers, kayakers, and hikers alike. For those interested in walking the loop around Jordan Pond, you’ll find yourself enchanted by the colorful foliage along North Bubble, South Bubble, and Pemetic mountains in the distance as you make your way around the pristine pond. Keep an eye out for wildlife during your hike, too. Jordan Pond was the first place I spotted a wild beaver in Maine!

  • Location: Acadia National Park in Bar Harbor, Maine

  • Difficulty: The loop around Jordan Pond is generally easy, although visitors are asked to walk on the designated boardwalks to protect wildlife, which can be narrow at times. One section of the trail also involves passing over some rocks and small boulders.

  • Distance: 3.1-mile loop

  • Elevation: 42 ft

  • Estimated time: On average, it takes about 55 minutes to complete this hike

  • Estimated price: Visitors must pay an entrance fee to Acadia National Park to access Jordan Pond. Fees vary based on the type of vehicle (private, motorcycle, etc.) and visitor (private, educational group, large group, etc.).


New Hampshire:

Arethusa Falls / Frankenstein Cliff Loop, Crawford Notch - The Maine Chick’s Pick

Nestled in Crawford Notch, the Arethusa Falls hike is still one of my favorite hikes to this day. The scenic waterfall and cliff views of the rolling White Mountains make the hard hike worth it!

  • Location: Crawford Notch Park, Hart’s Location, NH

  • Difficulty: Hard

  • Distance: 4.9-mile loop

  • Elevation gain: 1,637 ft

  • Estimated time: On average, it takes 3 hours and 8 minutes to complete

  • Estimated price: Free!



Deer Leap Overlook Trail, Killington - The Maine Chick’s Pick

The Deer Leap Overlook Trail is a 2.2-mile out and back trail. It is a short and steep hike with an amazing view from a giant rock outcropping. Enjoy the overlook of the north side of Sherburne Pass and nearby Killington and Pico peaks. The trail is considered moderate and you might have to climb over boulders so bring those hiking boots!

Note: The trail starts on the east side of the Inn at Long Trail on the north side of Route 4. There are other trails located across the street on the south side of Route 4 with a bigger parking lot.

  • Location: Killington, VT

  • Difficulty: Moderate

  • Distance: 2.2 miles out and back

  • Elevation: 492 ft

  • Estimate time: On average it takes 1 hour and 8 minutes to complete

  • Estimated price: Free!


Apple Picking

A staple fall activity in the northeast, autumn in New England would be incomplete without apple picking. Beginning in late August and running through late October, picking fresh, ripe apples off the trees in orchards around the region is an activity you absolutely must partake in, more because the New England ritual says so than anything else.

Despite it being a social norm, apple picking is actually quite a fun activity that people of all ages can enjoy! Whether you’re planning an apple picking date with your significant other or you’re taking your whole family out to make a memorable afternoon of it, here are some of our favorite orchards you should visit:

Randall Orchard - The Maine Chick’s Pick

1 Randall Rd, Standish, ME 04084

Located about 30 minutes away from Portland in Standish is one of my favorite Apple Orchards to visit: Randall Orchards. The orchard has a farm stand that sells all your typical fall goodies like apple cider, pumpkins, maple syrup, etc. I always like to get a mini apple cider to drink straight away!

What's a visit to the orchard without fresh donuts? Don't worry you can stop at the donut stand for fresh apple donut holes on the road to the orchard.


Orchard Ridge Farm - The ExploreHer’s Pick

236 Sebago Lake Rd, Gorham, ME 04038

Situated on 38 beautiful acres of hilly orchards and wooded forest, Orchard Ridge Farm is a family-owned u-pick orchard with an onsite market located in North Gorham, Maine. From u-pick apples, pears, and berries to local dairy, meats, and crafts, you can purchase a wide variety of fresh, delicious, and local products while visiting Orchard Ridge.

Open year-round, Orchard Ridge regularly hosts community gatherings, which guests can explore here. Whenever I get the urge, I order a small pizza from Orchard Ridge’s market (made to order) and never leave without a sweet treat; their selection of whoopie pies is delicious!

Images by Katy Ryan, @katyryan


Pumpkin Picking

The pumpkin picking season tends to begin in mid-to-late September, with some farms waiting as long as until the beginning of October to welcome pumpkin pickers onsite. Either way, you will have plenty of time to grab some pumpkins in time for Halloween!

Pumpkin Valley Farm, Dayton ME - The Maine Chick’s Pick

Pumpkin Valley Farm is a family farm located in the town of Dayton, about 30 minutes from Portland. The farm has a pumpkin patch to pick your own pumpkin along with many other fall festivities like a 6-acre corn maze and a petting zoo full of cute farm animals.



The autumn season brings plenty of festivals and fairs across New England. Fairs are a great opportunity for farmers to showcase their fresh produce and artists to sell their handmade crafts. The cool, crisp air makes it a perfect time for visitors to stroll through the outdoor markets and exhibitions and savor the last bit of warm weather before the cold winter ahead.

Fryeburg Fair - The Maine Chick’s Pick

The Fryeburg Fair takes place the first week of October from Sunday through Sunday. During this week-long event, there are plenty of fair festivities to enjoy. From rides and games to food and shopping, there's something for all ages.

The fried food and sugary delights are one of the highlights of going to the fair. As soon as you arrive you may catch a whiff of the sausage and vegetables sizzling on the grill, onion rings and fries bubbling in the fryer, and the sweet smell of the Sugar House.

As if all of the food stands weren't enough, check out one of the many exhibitions. Don’t miss the Specialty Foods Pavilion where you can find jams, salsas, and spices in a wide array of flavors. You'll also spot gourmet treats like homemade fudge, maple candies, and specialty chocolates.


Cumberland Fair - The ExploreHer’s Pick

For 150 years, the Cumberland County Fair has brought agriculture and entertainment together for public enjoyment. Taking place annually, the fair is scheduled to run during the last week of September this year, with all kinds of exciting events planned.

From ox-pulling to live music, pumpkin weigh-offs to burrito eating contests – and so much more – the Cumberland County fair is full of treats and delights of all kinds. My favorite way to enjoy the fair is by riding the Ferris wheel, eating my fill of French fries, and helping myself to cinnamon-dusted fried dough. I also quite enjoy visiting the livestock in between their contests. The horses are among my favorite animals on site!



Scenic Drives

Taking a scenic, leisurely drive through long, winding New England back roads is a relaxing and enjoyable way to take in the natural beauty of autumn. Whether you opt for a drive loaded with pull-offs and scenic overlooks or one that takes you along trestle bridges and under covered bridges, New England has a scenic drive worth your time this fall.


Cadillac Mountain at Acadia National Park - The ExploreHer’s Pick

Cadillac Mountain tops the list of destinations visitors absolutely must add to their itinerary when visiting Acadia National Park. For those who don’t have an interest in – or feel comfortable – hiking up the mountain, you’re in luck! Cadillac Summit Road is a three-mile drive that leads you to the summit of Cadillac Mountain, which also happens to be the highest peak in the entire park. Between May and October, vehicle registrations are required in order to access Cadillac Summit Road, and this registration is separate from the entrance pass you’ll need if you want to access the rest of Acadia. Visitors can purchase both passes at Once you have your vehicle registration in hand and you’ve begun making the trek along Cadillac Summit Road, you’ll notice there are several scenic pull-offs available to stop and enjoy the view along the way up. Once you reach the summit, you’ll find short-term parking available, as well as restrooms, a gift shop, and plenty of scenic overlooks. Cadillac Mountain is one of Maine’s most popular tourist destinations year-round, particularly in the summer and fall months. The earlier in the day you reach the summit, the better, if you want to do some leaf-peeping without mobs of tourists around.


New Hampshire:

Kancamagus Highway in the White Mountains - The ExploreHer’s Pick

Say hello to the Kancamagus Highway: one of the best foliage viewing areas in the entire country! Driving along Kancamagus Highway is probably the most popular fall sightseeing activity featured in this entire New England guide and for good reason.

This 34.5-mile scenic drive follows Rt. 112 in Northern New Hampshire through the White Mountains National Forest where travelers can enjoy breathtaking views of Swift River, Sabbaday Falls, Lower Falls, Rocky Gorge, and miles of colorful trees. Nicknamed “The Kanc,” this famous highway takes you far away from the comforts of city life. You won’t find gas stations, restaurants, hotels, shops, etc. along this drive, as those luxuries are only located at each end of the scenic byway. Instead, you’ll discover six campgrounds in the area and plenty of hiking trails to enjoy, should you decide to stop and stay awhile in the beautiful White Mountains.



Smuggler’s Notch State Park - The Maine Chick’s Pick

The Smuggler’s Notch scenic drive is a 3.5-mile long highway that winds through the Green Mountains of Vermont. It goes between the towns of Stowe and Jeffersonville. Drive through Smuggler’s Notch for breathtaking foliage sights where you can experience a tunnel of color. The park is full of picturesque forests and rocky ledges. If you are feeling up for it, stop at one of the many hiking trails along the way. The trails throughout the park offer excellent views of Smuggler’s Notch and nearby mountains like Mt. Mansfield, the highest peak of the Green Mountains.


Unique Perspectives

New Hampshire:

Loon Mountain Gondola Ride - The ExploreHer’s Pick

Say hello to Loon Mountain, the home of New Hampshire’s longest scenic Gondola Skyride! This 1.3-mile ride slowly ascends to the high-altitude summit of Loon Peak, all the while giving you a breathtaking 360-degree perspective of the rolling mountainous landscape around you.

Riding Loon Mountain’s Gondola Skyride during peak foliage is a lovely way to take in nature’s beauty during autumn. Once you reach the summit, you’ll have the opportunity to explore the high alpine world awaiting you at the top. When you’re finished hiking around, you can ride the Gondola Skyride back down for a final epic view of the colorful trees lining the rolling terrain. If you decide to ride Loon Mountain’s Gondola Skyride, your best bet is to buy your ticket(s) online ahead of time so you can skip the line in person. Ticket prices vary year-to-year, but the 2022/2023 cost is $25/adult. Purchase your ticket(s) here.



Penobscot Narrows Observatory - The ExploreHer’s Pick

Situated in the heart of Midcoast Maine, the Penobscot Narrows Bridge is a 2,120-foot-long bridge that connects Verona Island to mainland Maine (via the town of Prospect). This cable-stayed bridge is vital for auto traffic, but it has also become quite the tourist attraction in coastal Maine. The Penobscot Narrows Bridge features an attached observatory that is, interestingly, the tallest public bridge observatory in the world!

Considered the crown jewel of coastal Maine, visitors are highly encouraged to ascend to the top for spectacular 360-degree views of the Penobscot River, Penobscot Bay, rolling mountains in the distance to the west, and the beautiful wooded neighborhoods lining the water’s edge. While this view is incredible to witness year-round, seeing it during peak foliage is an absolute must. Colorful trees stretch across the landscape as far as the eye can see!

The Penobscot Narrows Observatory is a great family-friendly activity suitable for visitors of all ages. Cost varies by age and state residence, but all tickets are under $10/person and can be purchased online here.


New Hampshire:

Scenic RailRiders- The ExploreHer’s Pick

Located in Concord, New Hampshire, Scenic RailRiders is yet another unique way to enjoy the beauty of fall in New England. Once an abandoned railroad track, this rail-trail system was transformed into a tourist attraction in 2019 whereby passengers ride custom-made four-wheel rail bikes along the established tracks. Designed for passengers of all ages, the rail bikes are connected together in sets of two or four, with each bike outfitted with its own pedals, seatbelt, and disc brakes. No steering is needed, as these rail bikes roll easily along the flat railroad tracks once the pedals are in motion. Once passengers are safely strapped in, they are asked to follow their group instructor and pedal along the tracks for a nearly two-hour tour. Along this ride, the tour loops around 6.4 miles of scenic and diverse landscapes. From tranquil river views to open farms, wooded neighborhoods to old bridges, passengers enjoy a pleasant and picturesque New England tour on this fun, family-friendly activity. To pedal the rails with Scenic RailRiders, reservations are required and slots book up fast! Be sure to book your two-seat tour ($86) or four-seat tour ($148) well in advance to claim your desired day and time. This unique activity is available most of the year, but autumn really is the best season to take in nature’s vibrant foliage and cool, crisp weather!


New Hampshire:

Cafe Lafayette Dinner Train - The ExploreHer’s Pick

Perhaps the most unique fall sightseeing activity featured in this guide is the Cafe Lafayette Dinner Train, New Hampshire’s premiere dining experience! Based in Woodstock in the scenic White Mountains, this 1950s train boasts vintage rail cars that have been completely restored and renovated to accommodate fine dining. Inside each rail car, tables and chairs line the interior in clusters, each grouping comfortably fitting four guests. Running May through October each year, Cafe Lafayette Dinner Train treats passengers to a five-course meal while traveling on a two-hour ride 20 miles roundtrip through the woods, over three trestle bridges, by a Christmas Tree farm, and through a golf course. During the ride, guests are served bread with butter, a modest starter salad, an appetizer of their choosing, an entree of their preference, and a set dessert while slowly covering the 20-mile trip. From personal experience, I can say the food aboard is quite exceptional. My favorite dish was the baked brie appetizer wrapped in phyllo dough with a mixed berry puree! While the food is divine, the views are even more incredible! For anyone intrigued by this unique sightseeing experience, I highly recommend you board the train in the fall and make your reservation ahead of time by booking here. Prices begin at $95/person (varying according to seat assignment) and passengers must dress in business attire according to Cafe Lafayette’s dress code. Trust me when I say the cost and dress code are worth it – the views are quaint, relaxing, and unbelievably beautiful!


Fall Products to Enjoy

Our Favorite Fall Products

Petalage Florals - The Maine Chick’s Pick

Fall is a great time to refresh your space and transition to the new season with warm autumn hues - an easy way to do that is florals! Petalage Florals is a women-owned floral studio by Michelle Glassman. Her business specializes not only in weddings and special events but also in grab-and-go floral arrangements and gifts.

One of my favorite types of flowers is the dried kind so they last forever! You can find dried floral hoops (pictured below), wraps, and mini dried sticks at Petalage Floral. They are made locally sourced with dried and preserved flowers from Maine farms.

For now, you can order your blooms on Petalage Floral’s online shop and soon you can go in-person to the relocated shop opening in South Portland, Maine this November.

Image by Marissa Elise Photography via Petalage Florals

Modern Chandler Candle Co. - The ExploreHer’s Pick

When it comes to readying your home for a new and festive season, candles are a staple in just about everyone’s household. Not only do they smell amazing, but candles also make simple yet lovely decorations in any room. Even better, there are countless fragrances for every season of the year – like sea salt for summer and pine for winter – and autumn is no exception!

Portland, Maine’s female-owned candle company Modern Chandler Candle Co. is one of the best small businesses in the Greater Portland community to shop for all natural, non-toxic, hand-poured candles. Modern Chandler sells a wide variety of scents, with an entire line dedicated completely to fall! A few favorites are Apple Orchard, Cranberry Bog, and Flannels Sheets.

You can shop Modern Chandler Candle Co. online or in select retail locations around New England!


Festive Drinks

One of the best parts about fall is the return of the pumpkin spiced latte (PSL). Just ask Starbucks! However, there are many other fall drinks worthy of your taste buds, and why not support the local community while expanding your palate?

Here are a couple of local cafés and drinks in the Greater Portland area to ring in the fall season.

Smoked Maple Latte from The Proper Cup - The Maine Chick’s Pick

500 Forest Ave, Portland, ME 04101

Fittingly named, The Proper Cup is where you get a “proper cup” of craft coffee and espresso. Made with in-house vegan syrup, you can order a pumpkin spice latte or pumpkin spiced chai, however, one of my favorite drinks on the menu is the Maple Smoked Sea Salt Latte made with espresso, maple syrup, steamed milk, and topped with alder-smoked salt. It’s the perfect combination of salty and sweet!

Hours: Everyday 7:00 AM - 1:00 PM


A Dirty Chai from Smalls - The Maine Chick’s Pick

28 Brackett St, Portland, ME 04101

Fall beverages aren't limited to just pumpkin or apple flavors. If you're a fan of tea, then there's nothing that captures the essence of fall better than chai – an Indian tea infused with cozy spices like cardamom, cloves, and cinnamon.

And for coffee lovers, you can take it up a notch with a shot of espresso, creating what's known as a 'dirty chai'! In the photo, you can see my picturesque dirty chai from Smalls, a charming and relaxed café nestled in Portland's West End.

Hours: Everyday 8:00 AM - 8:00 PM


A big thanks to travel blogger The ExploreHer for partnering with me on this co-branded New England fall guide. For more content from The ExploreHer, visit



Welcome to "The Maine Chick," where I celebrate all things Maine, embracing the Maine way and living life to the fullest! While you can often find me exploring my hometown of Portland, Maine, you'll also catch me traveling around the globe. Follow along!

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