🧭 All Group Hikes - Summer Friday Hikes
*NEW* Fall Friday Group Hikes - Only $20, Including Pickup! (Select Dates)
*NEW* Fall Friday Group Hikes - Only $20, Including Pickup! (Select Dates)
✨ All group hikes with pickups are free with a MORE Membership.
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Updated Sep 2025
Join your host on these popular fall hikes! Pickup included.
WHAT TO EXPECT
Trip ratings are BEGINNER-to-ADVANCED.
See Destinations & General Trip Information below for ratings, gear, pickups and more.
- 10am Arrive at destination.
- ~2p Conclude trip, return to trailhead
- ~5p Arrive in NYC
*Schedule is subject to change.
IMPORTANT DETAILS
- Fall Group Hikes occur rain or shine, but will be canceled during real-feel days exceeding 100-degrees or snow forecasts exceeding a foot or more. Check Destinations below for weather forecasts.
- Confirmed Departures require 4 or more guests. Feel free to inquire about number of other guests who have booked in chatbox below.
-
All Fall Group Hikes are dog friendly.
- Suggested equipment: headlamps.
- Missed a trip? Let us know via the chatbox below and it may get added-back.
Here's where you're going
Storm King Mountain (Beginner-to-Intermediate)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is an INTERMEDIATE trail (see below for ratings) with some of the most epic views of the Hudson Valley, plus Cold Spring and Breakneck Ridge views across the river.
PRO-TIP
Approach the trailhead from the north side - it's safer. Consider Newburgh Brewing Company after.
HISTORY
New York physician Ernest Stillman donated the park's initial 800 acres (today 1,972 acres) to the Palisades Interstate Park Commission in 1922, hoping to protect land surrounding the Storm King Highway.
The park was the focus of preservation efforts in the early 1960s after a proposal by Consolidated Edison to build a hydro-electric power plant on the property. The Scenic Hudson Preservation Conference was formed by citizens opposed to the project, and the proposal was eventually dropped following a 17-year battle to preserve the park's natural state.
A 1999 forest fire at the park caused the detonation of unexploded ordnance that had been fired over 100 years prior by a cannon manufacturer across the river. Additional unexploded shells were also discovered that likely originated from a nearby West Point artillery range.
Mt. Tammany (Intermediate-to-Advanced)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is an INTERMEDIATE-to-ADVANCED 4-mile loop (see below for ratings) with jaw-dropping views of the Delaware Water Gap.
PRO-TIP
Consider visiting the Lakota Wolf Preserve after.
HISTORY
The forest is named after Charles Campbell Worthington, who, throughout the late 1800s, purchased 6,000 acres (24 km2) of land of both sides of the river, including parts of Mount Tammany. His intent was to create one of the premier deer hunting preserves in the county. He would name this estate Buckwood Park.
Balsam Mountain (Intermediate)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
PRO-TIP
Shorten your hike by doubling back vs. doing the loop.
HISTORY
In 1885, political machinations by the Ulster County delegation to the state legislature led to the Catskill counties being included in the newly created Forest Preserve along with the Adirondacks. Tax-delinquent lands, many of them abandoned by loggers and tanners who had taken all the harvestable timber, which had become the county's by default were transferred to the state as a way of settling the county's outstanding property tax obligations to the state. They were to remain "forever wild", with no timber being harvested again from them. In 1894, a more strongly worded version of the law was incorporated into the state constitution as Article 14.
Ward Pound Ridge (Beginner)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is flat, 3-mile BEGINNER trail (see below for ratings) perfect for slow walks and active kids.
PRO-TIP
You can primitive camp at this park.
HISTORY
Originally part of the Cortlandt Manor land grant, The Ward Pound Ridge Reservation began as farmland in the early 1700s. Today, it is a 4,400 acres county park located in the towns of Pound Ridge and Lewisboro in Westchester County, New York. It is the largest park in the county and offers diverse terrain, extensive hiking trails, nature programs, and recreational facilities. In 1925, Westchester County acquired over 4,000 acres to form Pound Ridge Reservation. It was renamed in 1938 to honor William L. Ward, the county park supervisor and key parks advocate.
Timp-Torne at Bear Mountain (Beginner-to-Intermediate)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is INTERMEDIATE 4-mile loop (see below for ratings) with abandoned ruins and jaw-dropping views of the Hudson River
PRO-TIP
Overnight parking permitted to access nearby primitive campsites.
HISTORY
In 1908 the State of New York announced plans to relocate Sing Sing Prison to Bear Mountain. Work was begun in the area near Highland Lake (renamed Hessian Lake) and in January 1909, the state purchased the 740-acre Bear Mountain tract. Conservationists inspired by the work of the Palisades Interstate Park Commission lobbied successfully for the creation of the Highlands of the Hudson Forest Preserve, stopping the prison from being built.
Mary Averell Harriman, whose husband, Union Pacific Railroad president E. H. Harriman died in September of that year, offered the state another 10,000 acres and one million dollars toward the creation of a state park. George W. Perkins, with whom she had been working, raised another $1.5 million from a dozen wealthy contributors including John D. Rockefeller and J. Pierpont Morgan. New York State appropriated a matching $2.5 million and the state of New Jersey appropriated $500,000 to build the Henry Hudson Drive, (which would be succeeded by the Palisades Interstate Parkway in 1947).
Stissing Mountain (Intermediate)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is an INTERMEDIATE 3-mile loop (see below for ratings) with a steep climb to the Stissing Mountain fire tower and epic views of the valley.
PRO-TIP
Learn more about this area at the American Museum of Natural History.
HISTORY
At the foot of Stissing Mountain lies the ancient Thompson Pond Basin, which formed nearly 15,000 years ago when a melting ice chunk created a depression or kettle. Over time, the kettle divided into three interconnected water bodies, including Thompson Pond, which forms the headwaters of a major tributary of the Hudson River. The basin's pond, cattail marsh, swamp and upland forest support a wondrously diverse array of wildlife.
Read more at the Nature Conservancy
Indian Head Mountain (Advanced)
WEATHER
Get a more detailed forecast here.
TRAILHEAD
SUGGESTED TRAIL
This is an ADVANCED 6.5-to-7-mile loop (see below for ratings) with a gradual climb to the top of Indian Head Mountain on the infamous Devil's Path trail, one of the most challenging trails in the NY. Plan for an all day trip. You will be exhausted, but you won't regret having made it to the top.
PRO-TIP
Don't forget to check out Black Chasm Falls in the Platte Cove Preserve.
HISTORY
The Devil's Path is a hiking trail in the Greene County section of the Catskill Mountains of New York, sometimes described as one of the more challenging trails in the New York Tri-state area.
Meet Al, your Trip Host
Hi, I'm Al and I'm excited to be your trip host for this trip!
I've been hosting hikes since 2012.
General Trip Information
SAFETY FORM
Updated Mar 2025
If you haven't already, you MUST complete or update your Safety Information Form below. Please fill out BEFORE your trip.
Your trip's rating is on its reservation page. If you haven't already, learn more about how we rate trips here.
As always no matter what pace you're able to go at, no one gets left behind.
Your trip host will also take breaks as needed. Your trip host is an experienced group leader and if conditions change or are different than what we expect, they are empowered to make adjustments as needed and will have final say on continuing or aborting any activity at any time should conditions become unsafe.
In the event the weather forecast makes our trip unsafe BEFORE your trip, you will be notified approximately 12 hours prior to your trip via email, text and/or a phone call with further instructions. Please make sure you have an updated phone number below. If you do not receive any notifications, your trip will occur like normal.
In the event the weather makes your trip unsafe DURING your trip, please follow all safety guidance from your trip hosts and/or park staff.
About Trip Safety Form
Why are you being asked all this information? Because you're getting a professionally hosted experience and we want you to have an awesome time. And that means Safety First, which may require medical assistance during your experience.
As a result, and as you can imagine, there's a lot of things that need to be anticipated for your safety. This form helps keep it all together for your trip host.
Although your information is kept confidential, it may be shared with your trip host in order for them to provide the best experience for you.
Please complete this form for yourself only.
AFTER YOU BOOK
Updated Mar 2025
All the details about your trip - including pickups, weather, itinerary and more - is already featured on the reservation page you booked from.
You will also receive a confirmation for your reservation and a separate Thank You email with the subject, "You've reserved a trip on Outerthere!" from us.
The sender will be "Al at Outerthere" and the subject of the Welcome email will be "Welcome to [name of trip]" and is only sent from info@ outerthere.com.
Here's what it'll look like in your inbox:
Please make sure you let your Gmail/iPhone know that this sender and email address are important.
If your trip is within 72 hours and you still haven't seen any emails from us, please check your spam folder or "newsletters" folder in Gmail.
In the meantime, if you have any questions, ask us in the chatbox here or reply to any email you've received from us.
PICKUPS
Updated Mar 2025
Traffic can sometimes affect pickup and travel times and meeting times are subject to change. You will be notified of any changes via text, so please make sure your contact information is up to date here.
There may be pitstops at your driver's discretion.
And finally, If you think you will be late to the destination or not able to make it for any reason, kindly notify us via text, chat or replying to this email.
Astoria Queens
Washington Heights, Manhattan
No Pickup?
If you think you will be late, kindly notify us via text, chat box on the site or replying to your trip confirmation email. Remember, other fam will be waiting, too.
ABOUT YOUR SHUTTLE
Updated Mar 2025
The vehicle for your trip will be a rented, privately-insured 15-seat passenger van with up to 460 cubic feet of interior space.
On occasion, your vehicle may be a rented, privately-insured 7-seat minivans with up to 144 cubic feet of interior space.
Your vehicle suitable for your trip and all associated rental and insurance fees are included as part of your reservation.
The interiors of your vehicle are cleaned and sanitized before every trip by your driver.
If you have any questions or concerns about your riding experience, don't hesitate to ask using the chat box below.
FREQUENT ASKED QUESTIONS
Can I cancel my shuttle ride after I've reserved it? As you may already know, we have an awesome refund & cancellation policy and your shuttle fee can be refunded with advanced notice.
However, if you change your mind on the day of your pickup; or you appear physically unable to ride in our vehicle (i.e. you're sick or intoxicated); or if your behavior is threatening or harmful to other passengers and you are not permitted to enter the vehicle by your driver, we unfortunately will not be able to refund you.
And hey, it's OK if you do not feel comfortable for any reason, and we won't take offense.
Is eating permitted in my shuttle? Yes. Please remember to take all your belongings and trash with you when you exit your vehicle.
Can I leave my stuff in my shuttle? Yes, however your driver may be making additional dropoffs, so please ask your driver.
Are pets allowed? Pets are allowed on most trips at the discretion of your trip host. Please make sure your pet is on a leash and not disturbing other passengers. Service stops will be included on most long trips.
WHAT TO WEAR
Updated Dec 2024
These recommendations are intended to help you select things you already have in your closet. You do not need to any new or technical gear to participate in this trip.
- TOP: Any top that you'd use to go to the gym. But dress in layers. The number of layers you bring should be based on whether you tend to run hot or cold. Below is a layers explainer video.
- BOTTOM: Flannel, denim, corduroys, tights whatever you already have in your closet works as long as it doesn't restrict movement. Same explainer video as above, but cut to the pants.
- FOOTWEAR: Sturdy, waterproof boots or trail running shoes that drain or dry quickly if they get wet. Below is a footwear explainer video.
- ACCESSORIES:
- Face covering.
- Insect repellent.
- Sun screen.
- Favorite sunnies.
- Trekking poles.
- Fanny packs/day packs.
- Small hand towel (optional and doubles as seat pad).
- Tote bag or day pack for your belongings and trash - please no littering. Use Trashmap.org to find the nearest trash bin.
WHAT TO EAT/DRINK
Updated Mar 2025
- Up to 1 to 2 liters of water, but you're welcome to bring more.
- Light snacks (pre-cut, pre-packed fresh fruit, dried fruit, trailmix, protein bars, veggie tray)*.
- Bring a lunch you can eat on the go (i.e. sandwiches, wraps)
*As a reminder, kindly take your trash with you, including fruit peels or cores. If it didn't grow there, it doesn't belong there.
Also, please submit the location of any trash bins you see to Trashmap.org. Help us keep parks trash free 🙏
ABOUT TRIP RATINGS
Updated Mar 2025
PACE
Everyone goes at their own pace and regardless of the pace you're on, you will never get left behind or be made to feel as though you’re slowing down your group. Whether you’re coming out for fitness or to just enjoy nature, the pace of the group can accommodate you.
BEGINNER PACE
Beginner pace trips and activities are for anyone physically active at least one to three times per week, including kids ages 5+.
Beginner hiking trips, for example, may cover 0 to 3 miles in distance where you will be walking across unpaved, natural terrain anywhere between 2 to 4 hours with plenty of breaks or an experience will include basic training.
Elevation is within 1,000 feet. And some features may require you to use your hands for leverage, balance, and even getting up or down.
Beginner pace trips are sometimes also labeled "Easy" or "Beginner-friendly" and in the case of water-based trips (i.e. kayaking), will be on calmer lakes and slow moving rivers. For beginner camping trips, we may go from trailhead to campground without backpacking. The pace will be slow to allow you to enjoy your experience to more solidly connect with others and nature.
Regardless of the pace you're able to keep, you will not be left behind and will be supported with demonstrations or other instruction until you're comfortable performing the basic activity.
Beginner pace trips are recommended for anyone who little-to-no experience, but wants to get more acquainted with that activity.
FAMILY FRIENDLY PACE
Like Beginner pace trips and activities, but with more consideration to kids and pets.
For example, other parents/nannies may be present and are happy to support you and your kid, activities are considerate of your kids attention spans and abilities, baby changing stops and areas are considered, area is walkable with carrier or stroller, etc.
INTERMEDIATE PACE
Intermediate pace trips and activities are a bit more challenging than Beginner pace trips, but completely doable for anyone active 3 to 5 times per week, including pre-teenagers.
An Intermediate pace trip may cover 3 to 7 miles, during which you'll be moving anywhere between 4 to 8 hours with breaks.
If you're participating in an Intermediate pace trip, you will be expected to have had some basic experience with this activity. You may already own some gear and/or equipment specifically designed for the activity and will be OK with unexpected weather.
And you may even be asked to support Beginners transitioning up to Intermediate pace.
Elevation is within 3,000 feet. And some features may require you to use your hands for leverage, balance, and even getting up or down. You'll feel it in your calves, quads, hams, shoulders, back, and arms next day.
Intermediate pace water-based trips (i.e. kayaking, rafting) generally assume you're comfortable in open water and/or with fast-moving water. Although you don't have to know how to swim, if you're participating in an Intermediate trip, it's recommended.
You will need to focus and stay alert at all times for your safety.
When you’re done, you may say to yourself you’ll never do a trip like that again, but afterwards, you’ll look forward to the next one.
These trips are recommended for anyone interested in stepping up their outdoor game or anyone about to start a training program.
ADVANCED PACE*
Advanced pace trips and activities are intended for anyone (including teenagers) who is active almost every day and could probably put together their own trip, but prefers going in a group with other Advanced fam.
They may cover 7 or more miles during which you'll be moving 8+ hours. Destinations, elevation and weather will be challenging.
If you're participating in an Advanced pace trip, you will be expected to have had some basic experience with this activity. You may already own all gear and/or equipment specifically designed for the activity and are knowledgeable with how to use it.
Advanced pace water-based trips (i.e. kayaking, rafting) will require you to comfortable in all types of water. You should know how to swim.
These trips are recommended for anyone thinking about DIY trips and need some additional guidance, anyone training to do epic, multi-day treks, and/or anyone interested in mixing up their normal weekly workout.
*Please be aware that some fam will attend an Advanced pace trip convinced that they are prepared. However, they may discover that they are not as prepared as they expected. Reasons why someone is going at a slower pace can include injury, dehydration, affected mental state, anything.
That is perfectly normal and in no way reflects a miscommunication or misunderstanding by anyone. Like it says in our Disclaimers, sh_t happens and your trip host can manage.
Depending on the circumstances, other fam in a group may be asked to support fam who are having a more challenging time than expected; and that's literally the advantage to joining group-based experiences like the ones on Outerthere - you may get asked to support each other and nobody will be left behind.
As a reminder, trips are safe spaces and no one will be made to feel as though they are being a burden or left behind.
SCOUTING
Scouting trips are meant for us to "test the adventure" (like breaking gadgets on purpose to see if they'll hold up to regular use) and figure out all the risks before planning a safe adventure for everyone else.
That said, since we won't always know what to expect, sometimes these scouting trips are very easy and even boring.
Or they are very challenging and extremely dangerous. We won't know until we try it.
Either way, they're fun for anyone who has already participated in Intermediate or Advanced trips, are open to anything and don't mind the unexpected inconveniences (weather, car issues, whatever) that come up on the way to a new experience.
These trips are recommended for anyone with advanced outdoor skills, lots of experience in the outdoors and a variety of outdoor gear.
SAFE SPACE REMINDER
Updated Mar 2025
We know we don't have to say this because you're all extremely mature and responsible, but this trip is a safe space. Please keep pets on leashes, don't smoke near crowds and don't drink to excess. Also, aggressive, unwelcome or inappropriate behavior will not be tolerated, period.
NEED TO CANCEL?
Updated Dec 2024
To cancel or reschedule your trip, please reply to the confirmation email you received after you booked your trip. That's it.
Don't forget to check your spam folder if you don't see it within a few minutes of making your reservation.
Learn what you're eligible for below:
UNDERSTANDING OUR NO QUESTIONS ASKED CANCELLATIONS POLICY
From the moment you make a reservation on Outerthere.com, there are a lot of people and processes involved to provide you with a safe, awesome experience and everything depends on reliable logistics and scheduling.
Occasionally, reservations sell out or need to be canceled. In such cases, we immediately notify you and offer you options, including rescheduling, credit towards other trips, donating your credit, gift cards or an immediate and full refund. That’s our policy.
In other cases, you may be running late, need to cancel, reschedule or switch your reservation. Here's how that breaks down for different types of trips:
ALL TRIPS
You have 24 hours (Members, 48 hours) after you've made your reservation to cancel a trip in order to be eligible to receive a full refund or credit, no questions asked. (See How Credits & Refunds Work below.)
In the event an unexpected circumstance causes you to cancel with less than 72 hours before your trip, any eligible refund or credit minus a 10% service fee will be processed within 21 business days upon request (Members will be processed next business day). Additionally, any add-on reservations for accommodations, camp sites, rentals and/or demonstrations are not eligible for refund or credit.
Any reservations made with any Pass are not eligible for refunds/credits if canceled less than 72 hours before your trip.
See How Credits & Refunds Work below. Reply to your confirmation email for faster service.
LATENESS
Your trip host and/or driver will notify you if they are running late to your meeting location and/or pickup. And if you are running late to a trip or pickup, please notify us and/or your trip host that you're running late, too. Your trip host may be able to wait at their discretion. Thank you.
If you are not able to make it to the meeting destination at the meeting time and miss your trip host and the group, we're sincerely sorry. That sucks. Especially after everything you went through to get there. And we know you don't need any more bad news, but you are unfortunately not eligible to reschedule or receive a credit* or refund for that trip, regardless of the circumstances. This includes Members.
DIRECT SHUTTLES AND MULTI-DAY TRIPS
You have 14 DAYS (Members, 10 days) before your trip to cancel a direct shuttle ride or multi-day trip in order to be eligible to receive a full refund or credit, no questions asked.
You have 10 DAYS (Members, 5 days) before your trip to cancel a direct shuttle ride or multi-day trip in order to receive credit for that trip.
- You are not able to book the same or different trip to replace any trip booked with a Sampler Pass.
Reply to your trip confirmation email for faster service.
HOSTED/GUIDED DAY TRIPS
You have 10 DAYS (Members, 5 days) before your trip to cancel a day trip by any trip host in order to be eligible to receive a full refund or credit, no questions asked.
You have 3 DAYS (Members, 1 day) before your trip to cancel a trip by any trip host in order to receive credit for that trip.
- You are not able to book the same or different trip to replace any trip booked with a Sampler Pass.
See How Credits & Refunds Work below. Reply to your trip confirmation email for faster service.
HOW CREDITS & REFUNDS WORK
Your credit is usable to reschedule the same trip, book a different trip, add on an amenity for a current or future trip and/or to purchase a Membership, Pass or Gift Card. But please note that your credit will expire after 90 days if not used. So, use it! Most credits are issued within 1 business day. Most refunds are processed within 5 business days (1 business days for Members).
DISCLAIMERS
The owner and operator of this website and its affiliates, partners and listed hosts reserve the right to change or cancel any itinerary or service at any time due to insufficient enrollment, bad weather conditions or other reasons without penalty.
a. If your reservation is cancelled due to inclement weather, dangerous conditions, a catastrophic disruption to a tour operator’s business, and/or public health emergencies, your reservation can be rescheduled, or your deposit will be credited or refunded, no questions asked. Weather-related cancellations are at the sole discretion of your trip host, not you or your weather app. And unless otherwise communicated, all trips occur rain or shine. That said, inclement weather, dangerous conditions, and/or public health emergencies are always a possibility on any outdoor activity, so there is no rescheduling or refunds during your trip or after you've been checked in.
b. In the unlikely event of a life-threatening emergency, participants may be liable for any rescue or evacuation costs incurred either on their behalf or as a result of their actions - depending upon trip location.
c. The participation of any person on any trip/program is continually subject to the discretion of your tour operator, Guides and/or Hosts.
d. No guarantees are made that you will enjoy your experience, including transportation, equipment rentals, destinations, schedules, accommodations, meals and/or trip host. The role of the hosts, guides and other operators is to use their judgement and experience to share with you a rewarding experience. If inclement weather, dangerous conditions and/or public health emergencies creates an unsafe experience - including any unexpected delays - a trip host/guide is empowered to change your schedule, itinerary and/or over planned experience. If time allows and your experience is deemed safe again, your host/guide is empowered to continue with the original experience schedule/itinerary. There will be no refunds, credits or rescheduling if any part of your experience is changed to accommodate safety.
e. If you believe your host/guide to be unprepared, exercising poor judgement or behaving in an unsafe or inappropriate manner, please contact us by replying to your Welcome email at any time to discuss available options.
DISCLAIMER
Updated Mar 2025
TIME, DATE & DESCRIPTIONS POSTED HERE ARE SUBJECT TO CHANGE FOR ANY REASON. Any changes regarding your trip will be emailed and texted to you.
Be aware that your trip may contain "side missions". Learn more about Side Missions here.
And remember, that sh_t does sometimes happen, so please don't panic if your trip host doesn't stick to a schedule exactly. Think of it as everything happening for a reason, even if you don't know what the reason is right away 🙂
