Psyched About Travel

16 Free Things To Do In Woodstock, NY


If anyone had told me years ago that I would someday be travel blogging about my home town, Woodstock, NY I would have laughed my head off. – “No way!” After all, what we’re used to we tend to take for granted right? Well, after deciding to host travelers from all over the world I had to do a quick study on the best of what we have to offer visitors arriving for the first time. The more I thought about it the more I realized how many amazing things there are to do here. As a person who usually travels on a shoe string budget I decided to create a list of 16 FREE and ALMOST FREE things to do in Woodstock, NY. Some of these are seasonal as you’ll see, but anyway  here is the line up!  Oh,  – If anyone out there knows of something I may have forgotten, please feel free to share it. with everyone in the comment section below.


If you love nature, walking, and photography, you’ll be enchanted with Cooper Lake –  a peaceful woodland with a stunning landscape that will transport your soul to another world. It’s the largest lake in the Catskill Mountains and located in the little town of Lake Hill about a 10 min. drive from Woodstock. You cannot swim there since it is actually the main reservoir serving the neighboring city of Kingston, NY. However, the views are jaw dropping and it’s a wonderful place for walking, biking, taking photos, or setting up an easel to paint. If you have a dog, bring him along for the walk. Keep your eyes open as you may encounter a turtle, beaver, or  salamanders in the water. Bears also frequent the area, so be aware.  Though they are majestic and adorable if you see baby bears do not approach as the mother is always nearby and can be ferocious when guarding her cubs. There is no fee to walk at Cooper Lake. To get there from the town of Woodstock take Rt. 212 heading west past the Bear Cafe and over the tiny bridge where there is an intersection with a stop sign. Turn left onto Wittenberg Rd. and continue a short distance ‘ til you see a road going straight up hill which is Cooper Lake Rd.  Stay on Cooper Lake Rd. which will route you through some apple orchards and woods. You will eventually start going down hill and see Cooper Lake through the trees. Pull over to the right and park against the guard rail. Enjoy!


Coopet Lake, Woodstock, NY

  •           MUSIC: HARMONY CAFE

One block from the center of town you will find Harmony Cafe which has a live band on most nights starting at 8:00 or 8:30 p.m. with the exception of  Monday ‘s open mic.poetry reading. There is no cover charge, but if you go it’s always  kind to show your support by dropping a few dollars into the musicians’ hat. Its restaurant, called “Wock ‘n Roll” serves pretty good Chinese and Japanese  cuisine so many folks choose to have dinner while listening to the band.



From May til the end of Oct. you can find the Woodstock Flea Market in Mower’s field one block from the Woodstock Village Green (town center). This is a place that people of all ages enjoy and can find colorful treasures, new and second-hand items in most categories. Need anything? Come to the Woodstock Flea Market and find household items, semi precious gem stones, plants, clothes, old pop records, and much more. There is no entrance fee.


Woodstock Sunday Flea Market

Woodstock Flea Market


 If it’s a hot summer day there are a couple unspoiled swimming holes walking distance from town. They are not huge, but the water is over your head in the center and certainly roomy enough to swim around and cool off. To get there, take Tannery Brook Rd. just off of Rt. 212 by the corner of Joshua’s restaurant and walk down the little hill bearing rt.  Cross the bridge and on the other side look to the right and  you’ll probably see people swimming. You can go there, or make a left and walk along the brook til you see a beige colored apt. building on the right. Just past that house you will find cars parked on the left by the brook. See the spot there where the brook (called the Millstream) opens up forming a rounded pool perfect for swimming. I’ve included a photo of it below. Be careful if you walk in the water here as there is moss on the rocks which can make them slippery.



    Two women hikers toasting wine glasses at the top of Overlook Mt.

    At the top of the world

This is a popular and moderately strenuous hike with the trail head beginning at the top of Meads Mt. in Woodstock just opposite the KTD Buddhist Monastery. It’s a two-mile steady climb up a gravel road.  Upon arriving at the summit you will find the remains of the historic old Woodstock Mountain Hotel which feels a bit like an archeological ruin now with only the shell of the building left standing. Then there’s the fire tower, and a trail leading to a ledge where you can see fabulous views of the Hudson Valley, and the Ashokan Reservior. Beautiful sight in mid Oct. when the fall leaves are in full color, but also lovely May  through the summer. It’s a 5 mile hike round trip from the parking lot opposite the KTD monastery and the estimated time it takes is about three hours depending upon how long you want to spend at the top. Just a word of caution – This is rattle snake and bear country and though there are not a lot of encounters, they are there and there are some. There is no entrance fee to hike.


Only a few blocks from the Woodstock Village Green there is a lovely woodland forest trail along a babbling brook that both you and your dog( if you have one) can take. To get there just walk on the left side of Tinker St. heading in the direction of Bearsville and make a left turn onto Comeau Dr. right after the Woodstock Apothecary. Walk up the hill and almost before the top you’ll come to a very low stone wall on the left where there is a very small sign saying “Eastern Trail” . Enter there and enjoy!


photo of a man painting the KTD Tibetan monastery in Woodstock, NY

KTD monastery, Woodstock, NY


At the top of Meads Mt. in the town of Woodstock  you can visit the impressive Tibetan monastery, KARMA TRIYANA DHARMACHAKRA where classes and workshops on Tibetan Buddhism are held. Free tours are usually given on Sat. and Sundays at 1:00 p.m. but it’s best to call in the am just to be sure that the tour is on:(845) 679-5906 ext. 3. If you can’t make a guided tour you can usually visit the main shrine room which is a blaze of color – another must see. The hours are:

  •  Mon – Fri: 2:00 – 6:00 pm
  • Weekends If a teaching is occurring:
    Sat:  1:00 pm – 3:00 pm, 5:00 – 6:00 pm
    Sun: 1:00 pm – 2:00 pm, 4:00 – 6:00 pmIf a teaching is not occurring:
    Sat and Sun: 10:00 am – 12:00pm, 1:00 pm – 6:00 pm

If you happen to be hiking the Overlook Mt. Trail on the same day you can stop in at KTD on before or after as it is located directly opposite the entrance to the trail head.


On Saturday nights at 5:00 pm the you can attend the Woodstock Library Cultural and Public Affairs Forum at 5 Library Lane just one block from the town center. Programs include poetry, book readings with well-known authors, comedy, music presentations and timely social/ political issues. Admission is free and you can check out the current schedule at Woodstock Library Forum

  •             GALLERY HOPPING

From the Woodstock Village Green (town center) you can go from one gallery to another. Check also for exhibits at the Woodstock Artists Association & the Center for Photography in Woodstock which are both located on Tinker St.



If you happen to be in Woodstock on a Wednesday don’t miss the Woodstock Wednesday Farm Festival where you can buy fresh produce from local farms, have dinner outside at picnic tables while  listening to live folk and contemporary music. Save your appetite for the best falafel in the US made by Abba – look for the line up at her tent! Sometimes if you’re lucky you can also snatch up some home-made strawberry shortcake ($5.00) in June. No admission fee to the market, only the cost of the edibles. The Farm Festival usually begins around the end of May and runs weekly til the end of Oct. Happy feasting!

This is an out door flea market with a table displaying fresh vegetables and fruit

Fresh Produce at the Woodstock Flea Market



 During July and August Shakespeare plays are held Fri., Sat., & Sunday evenings outdoors on the beautiful lawn of the Comeau property – only a couple blocks from the center of Woodstock. Suggested donation is $5.00  Bring a blanket to sit on or light weight folding beach chair. If you’re walking from the Woodstock Village Green stay on the left side of Tinker St./212 and turn left onto Comeau Dr. just AFTER the Apothecary. Go all the way to the top of the hill and you’ll the stage set on your left. There’s a large parking lot just opposite the site. For the 2015 performance schedule go to :  Woodstock Shakespeare Festival



Every Sunday afternoon from 4:00 p.m. – 6:00 p.m. the Woodstock Drumming For Peace Circle takes place on the Village Green. Join in, listen and dance to the drums if you like! Of course this is totally free and fun to experience!



Beginning around the end of May and running through Sept. you can enjoy enjoy free musical entertainment suitable for all ages on the Woodstock Village Green. The Woodstock Summer Concerts On The Green are scattered throughout the summer, usually on Saturdays and run from 1:00 to 5:00 p.m. if it’s not raining. Check out the 2015 schedule at: Woodstock Summer Concerts On The Green


On weekends during the summer months you can listen to live performances of classical music  at the Maverick Concert Hall, a rustic, magical half indoor, half outdoor theater in the woods. If you sit in the outside section in the back there is no ticket charge although they will ask for a donation (optional last time I checked). If you attend an evening concert bring some mosquito repellant and a folding chair. Concerts may be held at different times on Fri. Sat. or Sunday so check the schedule to be sure: Maverick Concerts Schedule




    Once a year over the Labor Day weekend the Woodstock Museum holds its FREE film festival with films guaranteed to stretch your edges. They are submitted by film makers from around the world and relate to a specific theme chosen each year by WM founders, Nathan Koenig and Shellie Lipton. Film showings include a Q & A afterwards with the visiting film maker and generally begin Fri. night, continuing through Sunday. In between films you can have sinfully delicious home-made deserts, drinks, other goodies in the little outdoor cafe or have a seat by the Native American Tepee a couple yards away. Donations are encouraged (gift what you can) to help make the festival possible. The Woodstock Museum is located a few miles outside of Woodstock. For info. on this year’s free film festival schedule and the Woodstock Museum’s other events see: Woodstock Museum Free Film Festival

Flaming sunset at the first bridge over the Ashokan Reservior

Flaming sunset at the first bridge over the Ashokan Reservior


    I was debating whether or not to include the Ashokan Reservoir here since technically it’s not in Woodstock, but the scenery is so spectacular that I would feel guilty about leaving it out AND it’s close enough – only a 20 minute drive from town, so if you have wheels this is one of those “Must Do’s” for everyone who spends any amount of time in the Woodstock area: The Ashokan Reservoir is an awesome beauty in all seasons. There is no entrance fee. Bring a camera and if it’s fall or winter, an extra scarf and warm jacket since it can be windy. There is is foot path/road over the reservoir where you can walk, ride a bike, or roller skate. Sadly, no doggies are allowed, but if you go in the summer at sunset you will probably see deer and ducks. The graceful Canada geese congregate  along the sides of the path and in the water with their families just before sunset.

     Canada geese at the Ashokan Reservoir

    Canada geese at the Ashokan Reservoir

    HOW TO GET TO THE ASHOKAN RESERVOIR FROM WOODSTOCK  – From the Woodstock Village Green take 212 and get onto Rt 375. Go several miles all the way to the end and make a left on Rt. 28E.  Continue past the blinking light and just before the next regular traffic light the road forks. Take the road to the right (28A I think, but it’s not visibly marked) and continue under the big metal overpass. Keep driving straight ahead past the Woodstock Nursery Supply store. Make a right at the next fork by the Reservoir Inn restaurant. The road will take you to a bridge over the reservoir and in my experiences this particular location gets the best sunset views. On the other side of the bridge make a right at the next fork.  You will drive several miles passing the side roads of Vinegar Hill Rd. and then Tebelt Rd. Keep going straight ahead following the occasional signs to Olive Bridge and W. Shokan. Bear right at each fork in the road and you will cross a 2d bridge over a gorge where the water has been dammed up over what looks like large stone steps. Immediately after this bridge bear right and continue a  short ways til you see a paved unmarked road on the right that goes into the woods. Take that road which will bring you to a big round circular parking area. Leave your car there and follow the other walkers into the blue Ashokan paradise!

      The Ashokan Reservior


 If you happen to be in Woodstock on THANKSGIVING or CHRISTMAS, the town throws a wonderful festive party and celebration for both holidays with dinner included at the Woodstock Community Center on Rock City Rd. These events are made possible by gracious hardworking local volunteers as well as the shops and restaurants that donate delicious home cooked food. All are welcome!


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