Celebrating 100 years of adventure on the Appalachian Trail with ‘Grandpa Walking’

By Gary Bennett

Harvey Dennenberg, aka Grandpa Walking

This article appears in the April 17, 2025, issue of the Frederick News-Post’s “72 Hours” entertainment insert.

In 2025, the Appalachian Trail, the longest hiking-only footpath in the world, celebrates 100 years of measuring the skills, endurance and heart of thousands of intrepid adventurers.

Over 3,000 hikers attempt to complete the entire length in any given year. Only about one in four succeed. The successful ones are forever known as “thru-hikers” and are treated on the trail with the awe and respect they deserve.

Along with these remarkable thru-hikers, the AT also welcomes and tests the more modest among us: day-hikers, section hikers and “2,000-milers.” The latter are pretty amazing, too. They are the people who hike the entire distance of the AT but not all at one time and not necessarily all in one year.

From its humble beginning at a conference of likeminded hikers and outdoorsmen in March 1925 to today, the AT has provided what was once unthinkable: a continuous, 2,200-mile footpath, skipping along the tops of the Appalachian Mountains from Georgia to Maine. The trail was ultimately completed in 1937.

To be sure, the trail tests one’s mettle at every turn. The terrain is mountainous for its entire length, with an elevation gain and loss equivalent to hiking Mt. Everest from sea level and back 16 times. Hikers of all stripes grouchily complain about the PUDs — the seemingly “pointless ups and downs.” The trail passes through some of the densest wilderness in the U.S.

Harvey Dennenberg, right, on the AT

Grandpa Walking

Although not a thru-hiker, Annapolis resident and divorced father of three Harvey Dennenberg is as adventurous as they come. He has been alive for almost the entirety of the AT’s existence.

The 84-year-old hiking savant is a proud 2,000-miler. He completed the entire trail in sections, beginning at age 68 in September 2009 and finishing up in 2021 at age 80. He lectures about the AT and has written a book, “Maine’s Appalachian Trail: How Seniors Made Section Hiking Easier,” which is available on Amazon and other sites and is also part of the permanent collection at the Appalachian Trail Museum in Pennsylvania.

And, no, he is not the oldest to ever complete the trail. But he’s close!

Dennenberg, known as “Grandpa Walking” (because all hikers must have a trail name) credits reading Bill Bryson’s famous book, “A Walk in the Woods,” in 2000 as his impetus for taking on the AT. There was something special about Bryson’s account of attempting but failing to complete the trail with his overweight friend Katz that piqued Dennenberg’s curiosity. Could he do it? He began to think he could.

He had some hiking experience. In 1993 he bought a second home in Boulder, Colorado, and hiked the local trails in the summer. He did his first modest AT day-hike in 2003 and then some overnight backpacking in 2005.

He retired in 2007 and moved to Maryland. Living in Lutherville, he frequented the trails around Loch Raven Reservoir and even did some camping and hiking in Frederick County at Catoctin State Park. One early AT section hike took him and a partner across Maryland from Pen Mar Park southbound to Harpers Ferry over four days.

Harvey Dennenberg in the wilds of Maine.

Dennenberg began his AT journey in earnest in 2009 by driving to Maine and attempting to scale Mount Katahdin, the infamous starting/ending point of the AT that stands over 5,700 feet high, is often snow-covered and is always rocky and treacherous for even the most seasoned hiker. He failed on this attempt “off the couch,” but he was hooked.

Over the next 12 years, he completed the AT in all 14 states, often hiking with other seniors — 33 different partners at last count, several of whom were women.

Dennenberg counts these many hiking partners and how they helped him among his fondest memories.

“Lee and Randy taught me two-car, road-to-road hiking. Fred and Greg taught me about pre-planning and using spreadsheets to plan hikes. Big Ed, aka Joker, always got water for me when I was too tired to move. Jim, aka Chill, was always calm and collected and a great influence when I got frustrated.”

The hostel owners along the way were also great and always willing to help, he said. He fondly remembers the wonderful, full-body massage he received at Woods Hole in Virginia after nine days of hiking.

And the food! Hiking the AT is a study in deprivation, according to most, so when you get the chance to eat well, you take advantage of it. He remembers a sumptuous breakfast buffet at Mountain Harbour on the Tennessee/North Carolina border and savory meatballs and lobster rolls at another stop.

Not everything, of course, was sunshine and roses.

Harvey Dennenberg completing his last state — Pennsylvania

Heat and humidity were his worst enemies, sapping strength and ending hikes. “I had planned a solo backpack [trip] for three days and two nights in July 2011. I had to quit after eight miles and call my shuttle driver to come get me. I had stopped sweating and knew I was in trouble.”

Fording streams in Maine was particularly tricky and harrowing.

“The rivers and streams have strong currents, and the smooth bottom rocks are covered with moss,” he said. “I always made sure one foot was firmly planted before moving the other foot.”

Then there are the infamous White Mountains of New Hampshire and Maine. For large chunks of the trail, there are steep, almost vertical climbs and descents. In many places, you must “hike” hand over hand.

“Mahoosuc Notch in New Hampshire is the most difficult one mile on the entire AT,” Dennenberg said. “There are huge boulders to climb over and crawl under and gaps in the boulders to jump across. I spent a lot of time crawling.”

While never seriously lost, he agrees that poorly-marked or unmarked areas can be a problem, especially in wilderness areas. Being able to use a map and compass in addition to a GPS device can make the difference between staying on track and getting lost.

Dennenberg never had any run-ins with wildlife but cautions hikers to be vigilant nonetheless. Food must be hung and not kept in tents unless you want company from a hungry bear. Hikers should also watch out for moose, especially in Maine, as they tend to use the trail to get from place to place, just as we do.

But Dennenberg would do it all over again if he had the chance and recommends the AT to anyone who has the will and desire to test themselves.

Unfortunately, in 2023, Dennenberg herniated his L2/L3 discs hiking the Long Trail in Vermont and had to quit after the first day. He has not hiked since and fears his hiking days may be over.

Even if he never takes another step on the AT, Dennenberg will be forever known as a 2,000-miler and affectionately as Grandpa Walking.

A book by Harvey Dennenberg, aka Grandpa Walking, about hiking the Appalachian Trail in Maine

Gary Bennett is a longtime Frederick resident who spends his time hiking, biking, volunteering and providing childcare for grandchildren. He is married and retired from his career as a nonprofit marketing executive.

The Maine Squeeze: A summer trip here is delightful

By Gary Bennett

The West Quoddy Lighthouse in Maine

Thus article appears in the September 5, 2024, issue of the Frederick News-Post’s “72 Hours” entertainment insert.

It was the beginning of summer here in the “land of pleasant living” in 2022, and the heat was already oppressive. My wife and I wanted to get away to somewhere with bright, 70-degree days and cool, 50-degree nights. In other words, we wanted a Maryland fall but with beaches and ocean.

We’ve tried the Shenandoah Valley and the Poconos. Both are great, of course, but can’t deliver on beaches and ocean. Ocean City has the beaches and ocean but not the weather (or slower pace) that we wanted. Enter our Maine discussion! We decided to spend a week exploring the state.

First, let’s get our bearings. Maine is the northeastern-most U.S. state and the largest (by far) but least populated of the New England states. Maine is well known for many things: its jagged, rocky coastline; sandy beaches like Old Orchard and Ogunquit; colorful maritime history; picturesque lighthouses; fresh, tasty lobsters; enormous moose; seemingly never-ending white pine trees; Mount Katahdin, one end of the Appalachian Trail; and untouched natural areas like Acadia National Park.

We went into this trip wondering why one of Maine’s nicknames is “vacationland,” but after a few days, we wondered no more. Spending a week in Maine was perhaps the most satisfying vacation we’ve taken. Everything was just so perfect: friendly people, charming accents, quirky places with Native American-inspired names, remarkably fresh food, breathtaking scenery and a satisfyingly slow pace of life.

Largest lobster in the world at Taste of Maine

We set off for Maine in our comfy SUV in June 2022, heading up the East Coast on I-95 to make good time. We had already booked two stops at cozy bed and breakfasts in Kennebunk and Bar Harbor. Since our first Maine stop, Kennebunk, is about 9 hours driving time from Frederick, we decided to stay overnight in New York City and take in a Broadway show. The next day, we got up early and headed north into coolers temps.

Driving close to the coast, we passed the heavily industrial Connecticut cities of Stamford, Bridgeport and New Haven, home to Yale University. Cruising into watery Rhode Island, we passed by the picturesque state capital of Providence. We carefully made our way around metropolitan Boston and up the coast of New Hampshire, where we finally started to see traffic and the pace of life slow. We departed I-95, no longer wishing to make time, in favor of Route 1 to take in the sights, sounds and scents of small-town life.

The drive through New Hampshire only takes about an hour before you arrive in Maine, perfectly nicknamed on welcome signs as the Pine Tree State.

In another 30 minutes, we were in Kennebunk. Be advised there’s also a Kennebunkport, right on the ocean, of course, and made famous during two presidencies as the summer home of the Bushes. All told, it was a relatively easy 5-hour drive from New York City to Kennebunk.

In Kennebunk, we stayed in a lovely bed and breakfast called The Tides, located right across from Goose Rocks Beach, which is technically part of Kennebunkport and one of the best sandy beaches you’ll find on the Maine coast. We enjoyed almost three miles of soft, white sandy beach that offered incredible views of the Atlantic and some small offshore islands. The tidal pools that form are also a hit during the summer, making a great place to float along in a natural lazy river. This beach is about as family-friendly as it gets in the state and is a favorite to spend time on during the warmer months.

Our three days in Kennebunk flew by as we enjoyed the beach, strolling the beautiful little village and eating at cozy restaurants. As you might imagine, we didn’t starve. We delighted in delicious lobster rolls, wonderful blueberry pancakes with fresh homemade maple syrup tapped from nearby trees and, surprisingly, Texas-sized steaks and fillets. We rented bikes for a lovely excursion up the beach and through neighboring villages, making sure to get back in time to take in a startlingly red “strawberry” moonrise over the ocean at dusk (we’d wondered why folks were traipsing over to the beach with their flashlights in hand).

In Old Orchard Beach, just up the road from Kennebunk, we spent a day at New England’s largest beachfront amusement park, Palace Playland. It was like taking a step back in time. At this family-owned attraction, we enjoyed the old wooden roller coasters, midway-style rides, water slides, carnival games and Maine’s largest arcade. Exhausted after a day in the bright sun cooled by ocean breezes, we decamped back to our friendly Kennebunk B&B to plan our morning departure to Bar Harbor and Acadia National Park.

Boat tour along the rocky Maine coast

On our way, we couldn’t help but stop at Taste of Maine restaurant in Woolwich, about an hour from Kennebunk. There, we found two of the world’s largest lobsters waiting for us. An inflatable lobster, measuring 70 feet long and 12 feet tall, greeted us from the roof. And the “world’s largest lobster roll,” at 2-feet long and packed with over a pound and half of lobster meat, greeted us inside. We didn’t partake, but the views from the back deck were so incredible, we lingered longer than we should have. This place is a must-visit when in the area.

Bar Harbor is about 3 hours northeast of Kennebunk and 2 hours from Woolwich. Sunrise in the summer is at about 4:45 a.m., which can take a little getting used to, but the air is so crisp and cool, you might not mind rising early.

Bar Harbor is a resort town of about 5,000 people that swells to many times that in the summer. Think Ocean City without the boardwalk or crowds. Still, it didn’t seem crowded there when we visited.

Bar Harbor is synonymous with great wealth. Many summer mansions dot the town, and numerous Rockefellers were born here.

Goose Rocks Beach in Kennebunk

We enjoyed strolling the quaint but hilly town while window shopping and reading menu boards, gazing out toward the Atlantic at the many little islands that seem to stand sentinel to the mainland, and walking across the bay. That’s right! Bar Harbor gets its name from a sand and gravel bar that is only visible at low tide, allowing tourists, day trippers, picnickers and hikers to wander about a mile across the bay to lovely Bar Island. It’s not often you get to explore the sea bottom, so we made that trip a few times.

Bar Harbor is also home to a large portion of Acadia National Park, which includes Cadillac Mountain, the highest point in Hancock County. It’s Maine’s only national park and, naturally, the easternmost in the U.S. We took a pleasant one-day excursion up Cadillac Mountain and enjoyed breathtaking views of the Atlantic, numerous tidal pools carved out among the granite rocks and impossibly green forests. A network of carriage roads — a gift from John D. Rockefeller — meanders throughout Acadia, making it easy to get around.

Don’t forget to try the Winter Harbor/Bar Harbor Ferry, one of the best boat tours in Maine. While technically a ferry that shuttles folks back and forth between Winter Harbor to the north and Bar Harbor, this ride on a converted lobster boat is also a scenic tour. For 45 minutes, you get a guided tour of Frenchman’s Bay and several of the islands and landmarks that occupy it between the two towns. Along the way, you’ll get an up-close look at the awesome cliffs of Ironbound Island, the Porcupine Islands, Winter Harbor Lighthouse and usually some wildlife — ocean sunfish, seals, porpoises, waterfowl and even the occasional whale.

There is so much we didn’t see during our weeklong visit to Maine that we can’t wait to go back. After all, Maine is a relatively large state and we stayed mostly “down east,” as the locals say.

Prepare to be spellbound if you take our suggestion and make Maine your next summer vacation destination.

Ellen Bennett arriving in Kennebunkport

Gary Bennett is a longtime Frederick resident who spends his time hiking, biking, volunteering and providing childcare for grandchildren. He is married and retired from his career as a nonprofit marketing executive.