The Wallflowers live

A Tale of Two Woodstocks

I never know where to go when visiting a city.

The sources of information are as diverse as they are incomplete.

Yelp is good for restaurants – but doesn’t tell you about the latest openings or little known gems.

Thrillist – the jury is still out.

Instagram – if you’re a detective/stalker you may get a few nuggets of information but rarely does a picture guarantee a good time. Will I take a 15$ Uber Pool to Somerville because I saw a picture of an ice tea that looked good on instagram? Maybe..

Upon looking for a nice weekend getaway from Montreal, I fell on a Vogue article about Woodstock. Yes that Woodstock.

As a huge music fan, the appeal of visiting woodstock/saugerties – where the iconic festival took place, where Dylan once lived and the band created amazing music in big pink – was considerable.

And so we picked the most hipster/trendy looking hotspots to visit, packed up our bags and drove for 5 hours – Montreal to Woodstock and stayed at a nice airbnb.

It turns out there are 2 Woodstocks. The one you read about in high profile blog posts and glossy magazines, and the less accessible but more authentic Woodstock.

Visiting Woodstock’s main drag, “Main st”, you come across charming souvenir shops selling tie dye tshirts and 60s rock paraphernalia interspersed with hipster coffee shops, independent book stores and taco shops.

deli on main st in woodstock

It quickly becomes apparent that the attractions peddled by the likes of Vogue will last you half a day to discover, leaving you wondering what all the hype was about.

As an avid road tripper I’ve felt duped before, reading about the top 10 up coming cities or whatever, only to visit and find the “cool” spots span literally 1 city block.

Thankfully for us, our airbnb host, a divorced woman in her mid 60’s became our gateway to the real woodstock.

woodstock nightlife

bear cafe in woodstock

She pointed out hard to find watering holes where we could swim and get some sun, local restaurants where we could mingle with Woodstock originals and artist colonies unique to the area. Her own personal stories played out like a movie and made us feel closer to the true nature of Woodstock.

Our weekend was topped off by a very intimate Wallflowers concert at the Bearsville theatre. It didn’t matter that the crowd was full of baby boomers, in fact in made the experience better. These people were here to have a good time at their local concert venue without any pretense – it was pure fun.

The Wallflowers live

The Wallflowers in Woodstock

Prior to leaving we went hunting for Americana treasures at a community yard sale, the perfect end to a trip.

The lesson here kids is that when you travel seek out the authentic, the original. Special people are out there waiting to share their stories and memories are there waiting to be made…and then posted to Instagram!