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First Time Backpacking Trips And Guides Anyone Can Do

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Getting out there for the first time backpacking trips can be scary! It’s difficult to plan any kind of vacation, much less of the “off-grid” variety. The trick is to pick something simple, but… how do you find it in the first place?

There are plenty of places you can go that are naturally safe. Of course you will still have to pay attention to the little details, but at the end of the day, odds are you will pull off a great trip.

I’ve been backpacking for four years. I’ve seen my fair share of hard trips, easy trips, and anywhere in between. Since I started my adventure education degree (yes, they have those) I’ve been practically living outdoors. Most of my time has been spent in the northeast United States.

In this article, I’ll be introducing you to six New England backpacking trips that will set you up for success. Each of them are around 50 miles, easy to access, and have minimal elevation change. I do recommend that for each of these you ask an experienced backpacker to help you plan it.

How far should I hike?

The first time my sister went backpacking I took her out for four days over the course of 20 miles. Our primary goal was to help her feel comfortable in the wilderness for an extended period of time, and to teach her how to use her gear. I would recommend the same experience for you. I know you can do these trips, but it’s a good idea to have someone show you the ropes on a weekend trip before you decide to send 50 miles.

After you get comfortable in the outdoors, then try planning a trip for others. Take your family on a short 20 mile hike, too, before taking them 50 or more miles. Planning a trip for a family adds an advanced component to backpacking. All of a sudden, their safety is in your hands. This is why it’s good to go without them first, usually with an experienced friend.

A few words on safety…

These trips are intended to offer the safest learning environment possible. To put it simply, it’s okay to mess up when you plan them! BUT here are three things you can do on every trip.

The first is to leave a detailed itinerary with a trusted contact before you go. Record where you are going, how long you plan to be there, what you are bringing, and when you can be expected back. This way your contact can call search and rescue if something happens.

The second thing you can do is check the weather, then record it in a notebook to take with you. You can plan on getting some rain no matter what, so bring a raincoat and rain pants just in case.

Last, bring a good first aid kit. Throw it in a plastic bag for good measure. Oh, and one more thing – you don’t have to drop a lot of money on a hiking first aid kit. Just buy in bulk from a large pharmacy, then repackage a little bit of everything into your own container.

When is the best time to hike?

For any hike in New England you will need to avoid bug season and mud season. Putting it simply, don’t bother with springtime hiking unless you have some serious cabin fever.

July, August, September, and October are the best months for any of these backpacking trips.

The best time for swimming will be July and August.

The best time for cool evenings, cool mornings, warm days, and photography will be September and October.

Fall foliage is going to be out, making any of these hikes very scenic. Plus if you hate the heat and hate being cold, you get a moderate temperature without any bugs. The only downside is you will need to bring a few extra layers. You probably won’t want to swim either.

Any later than October will be too cold for your first backpacking trip. Winter camping takes each of these backpacking trips from an “easy” rating to an advanced rating. So don’t go. Save them for later!

6 First Time Backpacking Trips, Easiest to Hardest

Northville-Placid Trail Section, Long-Lake in New York 20 Miles

You want to go swimming? Perfect. You want to take it slow? Perfect. You are super worried about finding places to camp? This is definitely the place to start. The Northville-Placid Trail runs for 133 miles through the Adirondack State Park. BUT. There is a super easy section that runs the length of Long Lake.

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Not only is it easy to drive there, but if you have a friend with a car, have them park it at the end. This way you don’t need a ride – your hiking buddy is already helping you out. If you have to go it alone, you can make this trail an “out and back” trek. Just plan on hiking to the end of the lake and back.

Long lake is beautiful. It’s also versatile – you can do this same trip in a canoe, launching at the south end of the lake. The entire east shore offers lean-to camping and miscellaneous tent campsites. For trail conditions, see Northville-Placid Trail along Long Lake – New York (AllTrails).

  • Trail Type: Out and Back
  • Start: Northville Lake Placid Trail Head, Long Lake, 177 Tarbell Rd, Long Lake, NY 12847, (43.98452, -74.39849)
  • End: Same as above.

Section of the Vermont Long Trail

I’m including two sections of the Long Trail here. You can see Section Hike Suggestions – Long Trail Planning Guide for more details. I recommend the Williamstown route because it has super easy transportation and can be done at a leisurely pace. You can take two days to hike it, or you can take four. It’s up to you!

Then there’s the Manchester Center to Killington section. This is much longer, but the view from Mt. Killington at the end is stunning. A huge reward for hiking so far!

Williamstown/North Adams MA to Bennington VT 18.1 Miles

Manchester Center to Killington 49.8 Miles

The Monadnock-Sunapee Greenway in New Hampshire – 50 Miles

Apart from Mt. Monadnock and Mt. Sunapee, this is a pretty flat trail. You will get to practice planning a very scenic trip that has easy to find lean-to’s along the way.

Much of this greenway was formed because private landowners came together for it. You can bring a dog, but make sure you stay on the trail at all times. You can’t stealth camp, for example, since everything is on private property. Don’t worry – the designated campsites are already super nice.

Mount Monadnock requires a permit to park your car. Try to get in touch with the Sunapee Mountain Ski Resort prior to your trip to confirm parking. Mount Sunapee allows parking, but please call ahead of time to double check.

The trail runs through Washington, New Hampshire, with a general store to resupply if needed.

Water can be scarce at the campsites themselves. See the SuperMap and trail guide for current water sources. You’ll just have to fill up and filter along the way as you find water sources en route.

It could be a good idea to hike from Mount Monadnock to Mount Sunapee, South to North. The views from Sunapee are bigger and better, a fun way to celebrate accomplishing this hike.

There is no shuttle at this time between Mount Monadnock and Mount Sunapee. You will need to have a car at the end and a car at the beginning. Or, you can have someone pick you up on your last day and drive you back to your car.

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One last thing – I tried to plan this trip without the map and guidebook. It doesn’t work! You’ll have to visit the official website and see where these resources are sold. It will make planning way easier.

  • Trail Type: Point to Point
  • Start: Mt. Monadnock parking
  • End: Mt. Sunapee parking

Appalachian Trail in Connecticut – 50.5 Miles

  • Time needed to backpack: 5 days, 10 miles per day
  • Campsites: Ten Mile River Shelter, Mount Algo Shelter, Stewart Hollow Brook Shelter, Pine Swamp Brook Shelter, Limestone Spring Shelter, Riga Shelter, Bassie Brook Shelter.
  • Scenic Views: Ten Mile Hill, Ten Mile River, Indian Rocks, Saint John Ledges, Mount Easter, Great Falls, Prospect Mountain, Rand’s View, Billy’s View, Lions Head and Bear Mountain.
  • Recommended Book: Appalachian Trail guide to Massachusetts-Connecticut Paperback – February 15, 2019, Sue Spring
  • Recommended Map: Appalachian Trail, Schaghticoke Mountain to East Mountain [Connecticut, Massachusetts] (National Geographic Trails Illustrated Map)
  • Campfires Not Allowed.

With beautiful waterfalls and scenic overlooks, this is a good section of the Appalachian Trail (AT) for beginners. The coolest thing about planning a trip on the AT is the historical significance. It is the longest consecutively marked hiking trail in the world, extending 2,200 miles from Springer Mountain in Georgia to Mt. Katahdin in Maine.

The Connecticut section in particular is unique for remains from the iron industry. There used to be quite a few operations in the area, today overgrown by emerging forests.

When you plan this hike, sit down with a map and really consider where your favorite campsites will be. Measure out rough estimates of how far you will go each day. On a day with elevation gain, such as Prospect Mountain, hike less far. Make up for it on a flat day. The more practice you get, the more natural it will feel to pick campsites without planning first.

  • Trail Type: Point to point.
  • Start: Sherman at the New York state line.
  • End: Brook crossing at Sage’s Ravine, just north of the Massachusetts state line at Salisbury.

The Taconic Crest Trail in Massachusetts – 37 Miles

  • Time needed to backpack: 3 days at 12 miles/day, 4 days at 9 miles/day, 5 days at 7 miles/day. Dependent on your schedule, fitness level, group size, and group experience.
  • Campsites: See map for suggested sites.
  • Scenic Views: Berlin Mountain, Snow Hole
  • Recommended Book: N/a
  • Recommended Map(s): Available at specific local stores or directly through the TCT Hiking Club. See website for detailed locations. If you choose to order your map, do so several months early in order to start planning.
  • Official Website: The Taconic Crest Trail — Taconic Hiking Club
  • Patch! Trail Patches — Taconic Hiking Club

You will notice I rated this as slightly more difficult than the AT in Connecticut. As the AT is so old, you will probably find the National Geographic map to be much easier to navigate with. The AT is also extremely well marked.

The Taconic Crest Trail (TCT) is much younger than the AT, or even the Monadnock-Sunapee Greenway. Between tree blowdowns and other miscellaneous needs for trail projects, it could be a little harder to navigate the trail. Plus it’s probably less populated. You could prioritize this hike if you want some solitude.

This trail does offer some noteworthy perks! It is really close to Albany, NY – it would be pretty easy to fly into Albany, then drive the 45 minutes it takes to the southern trailhead. For us locals, I included this because it is located on the Mass/New York border. In case you live nearby it could be a really cool trip to check out!

Not much information is available online. Much like when you plan the Monadnock-Sunapee Greenway, you will find the information you need on the map you purchase.

Contact the TCT Hiking Club directly to determine water sources, campsite locations, trailhead parking regulations, and other hazards before you go. Plan to rely on a tent or tarp style shelter due to potential lack of lean-to shelters. And as always, tell a trusted contact your itinerary just in case of emergency.

In case you can’t secure two vehicles for your trip, see if anyone local can give you a ride. Maybe you have a friend who can help you out! This applies to any point to point backpacking trip.

  • Trail Type: Point to point.
  • Start: Park first car at the Southern Trailhead, 42.43726, -73.37483.
  • End: Park second car at the Northern Trailhead, 42.80987, -73.28858.

The 100 Mile Wilderness in Maine

  • Time needed to backpack: 10 to 12 days, 10 miles per day. Add 14 miles for Mount Katahdin. Stay at the campground if you go to Katahdin.
  • Campsites: See maps.
  • Scenic Views: Gulf Hagas, Mt. Katahdin
  • Recommended Book: Appalachian Trail Maine Book and Map Set, Ray Ronan, Maine Appalachian Trail Club
  • Recommended Map(s): Appalachian Trail: Maine [Map Pack Bundle] (National Geographic Trails Illustrated Map), 100-Mile Wilderness Map & Guide (Appalachian Mountain Club)
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At first glance this is one of the hardest sections of the entire Appalachian Trail (AT) – but wait! I picked this trail because it is extremely well marked. It also has very consistent, easily found lean-to’s. If there isn’t a lean-to available, there are certainly campsites.

Here’s a little known secret – the AT in Maine is likely the most well-maintained section of the AT. There are many stone steps, waterbars, and other signs that this trail will last for another hundred years!

Another big reason why anyone can do this trip is the people you can meet on the way will help you. Many hikers on this trail are thru-hiking the entire AT. Sit down with them for an evening campfire and listen to their stories. They have many to tell, and free advice to give. Some thru hikers will be just starting their hike, hiking south from Katahdin. Conversely, others will be hiking south to north. If you continue to Katahdin you can bear witness to a momentous end to their 2,200 mile journey.

Okay, here are some logistics. Don’t start at Katahdin – save the best for last! Instead hike south to north.

Another thing is you won’t be able to resupply. Any town shopping needs to be done before this trip starts, as there won’t be signs of civilization through this corridor. The last town before this section is Monson, which also happens to love hikers.

Third, Baxter State Park (where Mount Katahdin is) is the buggiest park I’ve ever been to. Bring a bug net shirt, bug net pants, and bug spray. The mosquitos should be taken seriously! The rest of the 100-mile wilderness can be moderately buggy, but not too bad.

The best time would probably be August. I wouldn’t hike in the fall because Katahdin can see snow as early as October.

Finally, my only disclaimer: Do not choose this as your first backpacking trip ever. It is a trip for people who are beginner backpackers, but not first timers. You won’t be used to being in the woods and it would be best to try one of the 20 milers for your first one.

  • Trail Type: Point to point
  • Start: ME 15, Monson
  • End: Officially ends at Abol Bridge. Continue to Mt. Katahdin, Baxter State Park. You might want to leave a car at both ends and hike with at least one other person. If no second car is available, it is possible to hitchhike back to Monson.

Closing Summary…

Whether you’ve been backpacking or not, we all have to start somewhere. Not only is backpacking fun, but it’s affordable. Not only is it affordable, but it’s versatile. There are many factors that make backpacking a dynamic activity. You can go on one trip, then repeat the same one later and have a different experience altogether!

To set yourself up for success, always leave a note with a trusted contact that says where you’re going, for how long, and when you can be expected back. Bring your map, guidebook, and a great first aid kit. Check the weather beforehand, making sure to pack a raincoat and rain pants while you’re at it. And last, don’t forget to invite a friend with lots of experience!

If you’re heading to New England, the time of year will matter for your trip. July and August are warm, with perfect swimming weather. Then again, September and October offer sweeping views of fall foliage. Either way you won’t run into many mosquitos!

Take a chance and plan one of these trips. If you have to fly in from far away, try a longer trip, but make sure you go with someone experienced. If you’re a local, welcome! Try out one of the 20 mile ones – my personal favorite would be the Long Lake section of the Northville-Placid Trail (NPT).

Remember, it’s okay to make some mistakes! A million people have had tough first trips then returned for more, much more prepared than before. I am positive that you can do any of these six trips. Now get on trail and have fun!

Samuel
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