Tag Archives: Top of the Hill Tavern

You’ll Want to Tarry at Jerry’s

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The above photo shows what one sees walking in the front door of Jerry’s Tavern and gives a good idea of what to expect inside. Those who haven’t experienced this great dive bar in the Northwest Industrial District of Portland, might wonder how a bar that’s been opened for only about eighteen months became “World Famous.”

But those who know owner Jared “Jerry” Benedetto and his wife, Lauren, and followed him when he opened Jerry’s Pizza (as a hobby) and talked about his future dream would not be surprised.  Besides, the description on the door about global notability doesn’t mention a timeline. (#1)

Jerry – a guy who pursues his dreams

One of my good friends who follows Thebeerchaser wondered about my tendency to write about a lot of stuff besides just bars and breweries. He asked if I had toned down my quest to visit new watering holes.

I pointed out my recent post about my newest discovery – Top of the Hill Tavern and my list of favorite dives in that post and assured him that my journey would continue. I then responded that after writing boring memos on legal management for 40+ years, the opportunity to address a broad spectrum of topics was compelling.

As an aside, my brother-in-law, Dave Booher, who has been a frequent Beerchasing companion, just sent me an article entitled, “The Best Dive in Every State.” Having been to about 435 watering holes in the last fourteen years including about 200 throughout the US, I devoured the piece with enthusiasm.

I then sheepishly told him that I’d only been to one on the list – Portland’s Reel M Inn Tavern – a unique spot known primarily for its roasted chicken and jo jo’s, but not for its dive bar trappings. (I then asked Dave if was ready for a road trip….)

Why Jerry’s?

Well, let’s start with just the ambiance of this small (approximately 750 square feet) space, which is filled with Green Bay Packer (Jerry), Chicago Bears (Lauren), Milwaukee Bucks, Chicago Blackhawk, Milwaukee Brewer and Wisconsin Badger (where Lauren got both her BA and MBA) pennants and gear. And it’s not store-bought stuff – most of it is from Jerry’s personal collection.

You’ll see photos of regulars, old beer signs (especially Hamm’s and Miller), an iced bucket of Miller High Life in bottles, untapped kegs sitting on a table and multiple TVs with games (generally not being watched except for Packer and Bear contests), Christmas lights which stay up all year and ……well, you get the picture. (#2 – #3)

In fact, Jerry’s brought back memories of one of my top-five dives in Portland I visited in 2012 – the Ship Tavern. (The Ship is about the same size, a Chicago Bears and Cubs bar, has sawdust on the floor and the front exterior is unforgettable.)

I learned about Jerry’s from my son-in-law, Ryan Keene and his dad, Ron, who both have offices nearby. Since the last time the three of us had Beerchased was in 2017 at the Labrewatory, we were long past due. (This creative enterprise was one of the casualties of the pandemic and closed permanently in 2020.)

We decided to meet for lunch which allows me to talk about another great feature of the bar – the food – a limited menu because of the small kitchen, but we loved it and it gets great reviews.

The prices are also surprisingly low – where can you get a cheeseburger for only $8, a hot dog with grilled onions for $5 or three tacos for $10? The sides are also dive bargains – chips ($1), fries ($2), chili ($3) or cheese curds ($4).

Ron and I had an outstanding meatloaf sandwich for only $10. Ryan dug in on the wings (6 for $11) and we shared their cheese curds with ranch dressing – a Midwestern tradition. (#4)

Great in a sandwich
A Midwest tradition

I’d never seen a meatloaf sandwich in a dive bar, but given Jerry’s Midwest focus, I assumed the inclusion of meatloaf in the menu was because some guy in Racine, Wisconsin created it in the 19th century.

But, in an effort to enlighten you, here’s what I discovered:

“The concept of meatloaf dates back to ancient times, with evidence of similar dishes found in various cultures around the world. One of the earliest recorded recipes for a meatloaf-like dish comes from ancient Rome, where a dish called ‘patina’ was served. Patina was a mixture of ground meat, vegetables, and spices, baked in a pie crust.” (Tastefood.com)

The Drinks

I had a sample of the Stevens Point Lager – a great midwestern beer and they have a reasonable tap list, but the flagship beer at Jerry’s is my favorite – Miller High Life in a bottle – the Champagne of Bottled Beer – born in Milwaukee in 1903 and flavored with Pacific Northwest hops. (See this article from Vinepair.com for the interesting story on the slogan.)

According to the personable Bar Manager, Ranessa Williamson-Callen – a Wisconsin native – they went through forty cases during the previous weekend.

Most dive bar aficionados would not hit their favorite establishment for a cocktail, but that’s again where Jerry’s breaks the mold. You can get a quality margarita, old fashioned, seven & seven, white Russian or Tom Collins. 

What will bring me back, however, is the chance to have one of Ranessa’s Bloody Mary’s – also to meet Jerry in person. I’m relying on a Spring 2025 article in Portland Monthly Magazine (I would suggest this quality magazine has probably not written up a dive bar previously.)

“But the can’t-miss star here is Williamson-Callen’s impressive Bloody Mary: a 20-ingredient mix, lager back, and a skewer of summer sausage, Muenster, pickled onions, olives, and a whole pepperoncini. It’s the best Bloody Mary I’ve ever personally consumed in Portland, full stop, and an emblem of the perfected-classics ethos that guides Jerry’s Tavern.”  (#5)

Fully loaded – best in Portland

Now besides beer and great cocktails, those looking for a mellow option can choose from several Jello-shots ($2) including strawberry, lemon or Malort.- a Chicago favorite.  And Ranessa, spent most of the time during our lunch working on preparing pudding shots ($5) (pumpkin spice) from scratch for the rest of October.

She has a delightful personality and we chatted while she worked on making the pudding.  (Fortunately, the television you see below with Stephen A. Smith pontificating was muted.) (#6)

The Other Stuff

Jerry’s has a great “juke box” with mostly country-western tunes on the “most played” list although it included numbers by Creed, 3 Doors Down and Sean Kingston (who will have time to write more songs while serving his three-year prison sentence). Surprisingly there were no selections by Meat Loaf.

There is an expansive patio immediately adjacent which also sees a lot of Miller downed on good weather days.

In short, Jerry’s Tavern is a wonderful dive bar and I will definitely return to meet Jerry and Lauren personally as well as downing one of Ranessa’s Bloody Mary’s. The following two reviews (and they are almost all positive) may help convince you that Jerry’s will, in fact, become “World Famous.”

“Jerry’s isn’t just a bar. It’s a cathedral of character…The man himself, Jerry, is behind the bar, slinging drinks like he was born for this. He’s part bartender, part therapist, part shaman. He could be my dad if he wanted to, but this morning he feels like my brother–the kind who’d bail you out of jail without asking questions.” (Yelp 12/1/24)

“This place looks like it’s been plucked directly from the Midwest and dropped in Portland’s NW Industrial area. It also looks like it’s been here for years, not days. It feels cozy and familiar without trying too hard. I have been following Jerry’s journey for the past few years.”  (Restaurant Guru – 2024) (#7)

Jerry’s dream was to not just to open a bar:

“…but a community space in the tradition of a great Midwestern bar. Or, as Benedetto puts it, ‘a place to gather when times are good, when times are bad, or any time for that matter.’ ”   (Oregon Live)  (Photo courtesy of Michael Novak/Portland Monthly magazine.)

He’s a dreamer.

So far, so good, Jerry and Lauren!

Cheers

External Photo Attribution

#1. Linked in logo – (https://www.linkedin.com/in/jared-jerry-benedetto-5a69a4180/).

#2. Yelp Reviews (https://www.yelp.com/biz_photos/jerry-s-tavern-portland?select=snWOH0M6WDbb9sp0dsHFhg)  miller lite

#3. Yelp Reviews (https://www.yelp.com/biz_photos/jerry-s-tavern-portland?select=Ngyf0LVcTCzgPXlREDj8hg).

#4. #Wikimedia Commons (File:Meatloaf on white plate.jpg – Wikimedia Commons) This file is made available under the Creative Commons CC0 1.0 Universal Public Domain Dedication. Author: Roundhere44 – 7 March 2016. 

#5. Public Domain – Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Bloody_Mary_2.jpg) L licensed under the Creative Commons Attribution 2.0 Generic license.  Author: goblinbox https://www.flickr.com/people/25977089@N00) – 15 March 2014.

#6. Yelp Reviews ((https://www.yelp.com/biz_photos/jerry-s-tavern-portland?select=h_PosqSFpag7lxZ7-JANZQ).

#7. Facebook Page (https://www.facebook.com/photo.php?fbid=10105147031135361&set=pb.22016580.-2207520000&type=3).

#8.  Portland Monthly (https://www.pdxmonthly.com/eat-and-drink/2025/01/jerrys-tavern-restaurant-bar-review). Courtesy of Michael Novak/Portland Monthly magazine.

Get Your Thrill at the Top of the Hill

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Those of you who follow this blog know that I write about both bars and breweries. Having posted reviews of 400+ since I started this retirement hobby fourteen years ago, my favorite genre is dive bars.

That said, while my wonderful wife loves breweries, dive bars are not on her dance card. (I might add, her definition of a dive bar and mine are quite different.)  One notable exception was on a 2016 road trip in California to Yosemite National Park where we spent one night in Sacramento and I persuaded her to raise a mug in the world’s most literal dive bar. 

Live Mermaids?!

While at the bar, I asked bartender, Jason, how the title of the bar was derived. He immediately responded, “Take a glance upward. You see that 7,800 gallon aquarium? (To put in perspective, that would be about 503 kegs of beers.) A few nights each week, we also have “mermaids” swimming in that tank.  Now do you understand how we got our name.?” 

A Recently Discovered Portland Dive , But First….

Before I tell you about the Top of the Hill Tavern, my newest dive on Portland’s east side, it may be worth reminiscing (at least for me) about some of my Oregon favorites. Our travel has taken us to bars and breweries throughout the US and even a few in Europe, but it seems the best are close to Portland. (By the way, it’s a wonderful place to live….)

https://thebeerchaser.com/2024/02/02/dont-jump-when-you-can-dive/

In Portland dives, the PBR, Hamms and Budweiser flow like a mountain stream cascading down the slopes of Mount Hood in early spring. (#1)

Sky Blue Waters

The photos shown below are my five favorites – The Ship (2012), the Mock Crest Tavern (2012), Gil’s Speakeasy (2017), The Standard (2018) and Yur’s Bar and Grill (2020). 

Yet, I can’t forget the Oregon Coast where at these five watering holes, the frothy head in your mug is like a wave at its foamy crest just before crashing onto the pristine white sand before receding for another cycle. (#2)

Thats when on a 2014 Road trip with two friends (Dave Booher and Steve Larson), we hit twelve bars on the coast in 2.5 days with these four making the all-star list in addition to the Desdemona Club (The Dirty D) in Astoria in 2012. 

The Sportsman Pub and Grub (Pacific City), the Old Oregon Tavern (Lincoln City), Mad Dog Country Tavern (Newport) and the Tide Pool Inn (Depoe Bay) garnered the other four top spots. (#3)

I had driven by the Top of the Hill numerous times – an inconspicuous building with a large parking lot, but no other businesses or homes around. My intent last March was to visit it with my long-term Beerchasing friend, Hillary Barbour.

But I messed that one up and told her to meet me at the Hi-Top Tavern which is only 3.6 miles away or a nine-minute drive from Top of the Hill. We enjoyed the Hi-Top, but it was a classy neighborhood bar and definitely not a dive.  So, we resolved, the next time we Beerchased to dive at the Top of the Hill.  (And it was worth it.)

I’m a fast learner, so I cautioned Hillary that we were going to the Top of the Hill in NE Portland – not the bar with the same name in Kaimuki, Hawaii or Babe’s Boys Tavern at the Top of the Hill in Upper Marlboro, Maryland. 

Similarly, we were not going to raise a mug at Top of the Hill Bar in Cork, Ireland or at North Carolina’s first microbrewery, the Top of the Hill Brewery and Restaurant in Chapel Hill (which even has its own Wikipedia page.)

And just to rub it in, Hillary admonished me not to show up at Top O’Th’ Hill – a family-owned American bar in Bridgewater, New Jersey, even though they have an outstanding butternut squash soup.

But as you can see below, we did meet on a Saturday afternoon at the right watering hole and joined a few regulars in relishing the “ambiance.”

I’ve known Hillary since shortly after her graduation from Reed College in Portland, when she was a Research Intern for the City Club of Portland and I was on the Research Board. She has had an impressive career including almost twenty years working on the staff of  recently retired US Representative, Earl Blumenauer. (#4)

Effectively served Oregon for thirty years.

Subsequent jobs have been in marketing and strategic planning for both private and non-profit corporations. Friends call her “Hill,” so perhaps the venue that day was appropriate.

Our server, Amber, who is a long-time employee of the bar said the owner is a nice guy and they have a good group of regulars – a community. Amber was personable and welcoming.

Most of the Top of the Hill reviews are positive and it seems that people really like this laid-back place. People appreciate the low-key atmosphere, the pool tables and old-fashioned beer signs, the friendly staff and karaoke on Friday and Saturday. And they have a good juke box. Two reviews sum it up nicely:

“I love this neighborhood bar! It has a cozy, comfy feel. All of the bartenders have made me feel welcome. Some of them have told me the owner is great to work for and that matters to me. It’s not fancy or extravagant by any means. Just a great place to hang out and get to know your neighbors. (Yelp 2023)

and

“Just a small trashy bar, but it’s my small trashy bar. The food is mediocre at best, and the pool tables are the worst I’ve ever played on, but the experience is like living in an episode of trailer park boys. Nobody is here to impress anyone, so everyone kinda lets their guard down more than usual, it’s a great place to meet people in a very casual setting.” (Restuarant Guru.com) (#5)

And you are not going to find less expensive pub food at many other places with a cheeseburger and side for $6.50 and large basket of fries or onion rings for $5.50.  A turkey sandwich with chips rings up for only $7.00 or a skad of wings for $5. Draft beers (a reasonable selection) are $5 to $6 with a buck off during Happy Hour.

Sundays are good with a rib dinner – four ribs with two good sides and bread for $18.  Want chicken instead of red meat, well the barbecued chicken dinner, sides and bread is the same deal. (#6)

I mentioned that Hillary graduated from Reed College – a liberal institution with outstanding academic credentials.  And the school made Portland headlines recently:

“Reed College students and alumni are grappling with the recent revelation that a campus security official provided federal investigators with personal information about a former student, ultimately resulting in his arrest. The disclosure has sparked significant backlash, particularly given the college’s reputation for inclusivity and its progressive values.

According to court records unsealed last week, FBI agents arrested Robert Jacob Hoopes, a 24-year-old Reed alumnus, on July 25. The records detail how Gary Granger, the college’s director of community safety, accessed an internal database containing personal information about students and alumni to hand over Hoopes’ name, address, and phone number. This cooperation allegedly occurred without a warrant or subpoena.”  (Reed College Campus Safety Newsletter)  (#7)

Granger was subsequently fired but given the misguided and unnecessary federal intervention to deploy the National Guard, Reed alums are wary that they may have been “identified.” 

There have been Blackhawk helicopters flying low over Portland neighborhoods and knowing Hillary might have been in that database, we searched the sky while walking to our cars. (After all she worked many years for a Democrat….) 

I have almost avoided political issues on this blog, but these times warrant a comment.

A Trump-appointed federal judge yesterday, temporarily blocked the National Guard deployment to Portland although there is no shortage of masked ICE troops at what have been largely peaceful demonstrations in the last year – basically some individual arrests by the Portland Police.

To put today’s protests into perspective, here’s what the data show:

“Arrests in 2020: 1,071. In 2025: Around 60 over the past four months.

Location in 2020: Across the city. Location in 2025: One to two blocks in South Portland.”   (Oregon Live October 5)

Portland faces significant issues – most notably homelessness. The violent and lengthy protests in 2020 were deplorable and our city still bears the scars, but that is clearly not the current situation.

Leave us alone to drink our good coffee and great craft beer and we will continue to work on resolving our problems civilly and locally. (#8 – #9)

Cheers

External Photo Attribution

#1.  WordPress generated AI image.

#2. Picsart.com AI (https://picsart.com/create/editor?category=miniapps&prompt=a+black+hawk+helicopter+with+an+x+over+it&projectId=68e1febafa021d2faa2b576d&app=t2i&version=1.86.2).

#3. Desdemona Club Facebook page (https://www.facebook.com/photo.php?fbid=275454077925770&set=pb.100063835381277.-2207520000&type=3).

#4. Public Domain – Wikimedia Commons (Earl Blumenauer, official portrait, 116th Congress 2 – Earl Blumenauer – Wikipedia) This United States Congress image is in the public domain. Author: House Creative Services, Kristie Baxter – 16 October 2019.

#5.  Yelp photos (https://www.yelp.com/biz_photos/top-of-the-hill-tavern-portland).

#6. Wanderlog.com (https://wanderlog.com/place/details/3441887/top-of-the-hill-tavern).

#7. Wikimedia Commons (File:EliotHallReedCollege.jpg – Wikimedia Commons). Licensed under the Creative Commons Attribution-Share Alike 2.5 Generic license.  Author: User.cacophony – 25 February 2007.

#8. Wikimedia Commons (File:Portland from Pittock Mansion October 2019 panorama 2.jpg – Wikimedia Commons). Licensed under the Creative Commons Attribution-Share Alike 4.0 International license. Author: King of Hearts – 28 October 2019.

#9. Picsart.com AI  (https://picsart.com/create/editor?category=miniapps&prompt=a+black+hawk+helicopter+with+an+x+over+it&projectId=68e1febafa021d2faa2b576d&app=t2i&version=1.86.2).

Try the Hi-Top Tavern – It’s a “Shoe*-in”

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With so many watering holes to explore just in Portland – other than the standard two visits I try to make as part of my Beerchasing protocol – I usually don’t return to an establishment I’ve reviewed.  There’s just too many great bars and breweries I still need to experience and too little time to accomplish this sudsy journey. (I decided not to quote Robert Frost…)

From 2011 until the pandemic in 2020, which caused a temporary hiatus in my pursuit, I had visited and reviewed 366 bars of which 119 were in Portland.  From that time onward, I’ve added about another fifty of which thirty are in the Portland area.

Although admitting, my post-pandemic count is not as precise, I believe that since starting this journey in fall of 2011, I’ve shown my face in 416 watering holes with 139 or 33% in the Rose City.

And my “return” to the Hi-top Tavern has to be qualified, because my first visit there was in the summer of 2012 when it was named Bottles.  https://thebeerchaser.com/2012/07/06/bottles-the-preferred-alternative-to-a-glass-ceiling/    

Bottles – originally a small Turkish import store – was a nice bar to sample the esoteric inventory of beers and wines which graced its shelves (between 450 and 500 different bottle beers with eight on tap), but it closed sometime in 2019.

Resurrection of the building came with the Hi-top in July 2019 by the Three on a Match Bar Group under the guidance of its principal, Ezra Ace Caraeff. 

I wrote about these bar revivalists in my recent review of the outstanding Holy Ghost Bar – one of five they own and operate besides the Hi-top, the others are the Old Gold, Paydirt and Tough Luck – all of which I still have to explore. (#1)

Bar Revivalists

Bar Revivalists

Memories

Before describing the visit to Hi-top, it gladdens my heart to remember the Beerchasing event at Bottles and County Cork, another Fremont Street bar, on the same day in July, thirteen years ago with colleagues from the Schwabe Williamson & Wyatt Environmental and Natural Resources Group.

Brien Flanagan, is still at Schwabe and a leader in that group. Patty Dost, Laura Maffei and Cheryl Rath, who now practice with other firms, also raised a mug at both of these bars – with dinner at Bottles after toasting Brien’s Notre Dame undergrad alma mater at the Irish Bar.

 All have had distinguished legal careers since that day and their expertise in air, water, hazardous waste and other environmental issues is notable. We’ve Beerchased on occasion since that day including a great reunion at Old Town Pizza in   with a number of other alumni of that group.

Bottles in 2012
Old Town Pizza in 2024

I was always happy that they indulged me when I would spout environmental stories and jokes from bar visits such as the old guy sitting next to me at a dive bar who asserted:

“You know it’s not pollution or industry that is harming the environment. It’s the impurities in our air and water.”

I also remember conveying the contemporary version of an old adage about personal development which got shrugs and moans from my friends:

“Give a man a fish and he will eat for a day.  Teach him how to fish and he will be dead of mercury poison in three years.” 

The Bar

Hi-top is not going to wow you with its layout or features.  It’s pretty generic although there are some neat smaller spaces, an expansive patio and a long bar with an impressive display of liquor bottles backing it. As stated in a Willamette Week article:

“The first thing you’ll notice in the old Bottles space is its bunkerlike atmosphere, which is both its biggest hindrance and its most admirable quirk. The ceilings are low and the floor plan is segmented into a variety of nooks and crannies, with garage doors and a vast expanse of whiskeys on offer.”

And while you may not come for a unique ambiance, the draw is the superb cocktail choices and an opportunity to taste Single Barrel Bourbon, evidently hand-selected by the staff and flown in from Kentucky.

You won’t see many beers on tap although I liked the concept in their bottled beers including four PBR Tallboys in a shiny bucket for $12 or a Miller High Life Bucket – four in a golden bucket for $12.

The food is also a plus with an excellent sandwich menu and quite a few small-bite and salad options – all at reasonable prices.  You might not be able to resist the $5 Chocolate Chunk Cookie (Brown Butter, Bourbon, Maldon Sea Salt).  I understand it pairs quite well with a PBR Tallboy

* You might wonder about the title of this post and the asterisk after the word “shoe.”  Two reasons – first, I’m doing a lot of reminiscing in this narrative.  And the last and one of the only times I’ve seen “Hi-top” used is in reference to the beloved Chuck Taylor Converse All-Stars. (You can pick up a new pair for only $64.99.) (#2)

A Classic Shoe

A Classic Shoe

As I’ve mentioned in the blog several times, my 1966 Oregon City High School TYV League Championship Team wore those sneakers with pride into the State Tournament where, although decimated in the first round by Lincoln of Portland, we made it to the consolation semi-finals where we lost by one point in overtime to Thurston.

My long-time friend and former teammate, John Davidson (#30) who went on to have an excellent run in hoops after high school at Grays Habor Junior College ,and I reunited last fall when he flew up from San Diego to have a free-throw contest at a local grade school. (None of the kids wanted to scrimmage with us.)

It was followed by Spanish coffees at Hubers’ Restuarant and an outstanding steak and martini dinner at Portland’s legendary Ring Side Steakhouse, where John worked part-time when he was a junior-high teacher years ago.

And to conclude on a Hi note, I have to mention my Beerchasing companion at the Hi-top – another long-time friend dating back to the 80’s (I think) when she was a research intern for the City Club of Portland and I was on the Research Board.

Hillary Barbour is one of the smartest and most industrious people I know, having graduated from Reed College, working for many years on the staff of Congressman Earl Blumenauer and then as the Director of Strategic Initiatives at Burgerville.

She is now

Hillary is a Beerchasing regular, having visited the Sandy Jug, the Jolly Roger, the Vern and Mad Hanna on previous Beerchasing experiences. (It was a coincidence that the first two initials of her first name are the same as that of the bar….)

Going to the Hi-top was actually inadvertent in that I thought we were going to another bar – the Top of the Hill Tavern – a classic dive on NE Glisan only 3.6 miles or eleven minutes away. 

I’d driven by this bar a number of times and thought it would be a great place to add to my list but got confused with the name and address and gave Hillary the NE Fremont address of the Hi-top instead. (We agreed to a future visit to Glisan Street.) (#3)

Hilltop Tavern – A future visit awaits….

In Conclusion

While the Hi-top was an okay neighborhood bar and evoked a lot of great memories, rather than return, I’ll try Three-on-a-Matches’ two other bars – the Old Gold and Pay Dirt – to see how they compare.

And in a final tribute to my Beerchasing colleagues – a bar joke:

“An environmental lawyer and a non-renewable resource walk into a bar and sit down for a couple of pints. After a while, the non-renewable resource orders two more beers. The bartender turns to the lawyer and says, ‘I’ll serve you, but not your friend, he’s getting wasted'”

Cheers

External Photo Attribution

#1. Three-on-a-Match Bar Group (https://www.threeonamatchbars.com/).

#2. Public Domain – Wikimedia Commons  (File:A classic Black pair of Converse All Stars resting on the Black & White Ed. Shoebox (1998-2002).JPG – Wikimedia Commons).  I, the copyright holder of this work, release this work into the public domain. This applies worldwide. Author: Hadley1978 at English Wikipedia – 18 November 2006.

#3.  Yelp site for Top of the Hill Tavern – (Photos for Top of the Hill Tavern – Yelp). Photo by Mark S. – July 28, 2008.