Adult Dinner Tour #1 – Island Pond

By: Tabitha Armstrong | 09.30.18

Friday Night Live Event in Island Pond 2018The town of Island Pond has seen an incredible transformation over the last few years. This little border town has come back to life through the hard work of its community members.

No longer just a snowmobiling Mecca, the addition of community music events, shows, town wide celebrations for holidays, and town activities to keep the community involved have filled area social calendars from spring to snowfall and beyond.

With this rejuvenation has come a number of Island Pond Restaurants, serving delicious food. The best part is – all have different options and all are in walking distance from each other, making Island Pond a perfect spot for an adult dinner tour. (What is an ‘adult dinner’?)


Take the Island Pond Dinner Tour

(Disclaimer – If you take our adult dinner tour, keep the receipts from all three restaurants, take a picture of all three showing the restaurant name and the date – the same date must be on all three – and submit them to our Facebook Page to be entered to win NEK Restaurant Gift Certificates)

Click on the links to view our full reviews of each restaurant and their menus.

KT Ray's on the Pond Restaruant in Island Pond - out door seating on the patioIsland Pond, Vermont (located in the middle of Brighton) is a small town with character. Its railroad roots are evident in its downtown architecture and the layout.  Restaurants are in easy walking distance from each other, summer concerts take place right in the middle of them all, winter activities are organized on the pond and throughout town, and free parking in downtown lots makes for easy accessibility.

We suggest parking next to the Essex House as this is the first stop on our tour. Parking is also available at the other end of the street if the Essex House is busy, or you prefer to start the tour at Hobo’s Café.

The Essex House Tavern is located in a building that has served as a hotel to the area off and on since the early railroad days. The fully remodeled dining room and bar has an industrial vibe, a great reflection of the town’s railroad past.

We love starting our Adult Dinner here because they have the perfect appetizer menu.

Maple French fries with pretzel salt from the Essex House Restaurant in Island Pond vtStuffed mushrooms filled with seasoned sausage and bubbling cheese are a must try! These tasty morsels are perfect for starting off a night of culinary selections without getting too full. We are also fans of their French fries served with a signature maple glaze and pretzel salt – a refreshing change from the traditional favorite. Among other appetizer choices for the first course of your dinner tour are an assortment of wing flavors, Thai skewers, their signature I.P Fish Balls, or a regional favorite – poutine.

Maple cocktail from the essex house tavern in Island PondThe cocktail menu at the Essex House is something to see. Though it changes throughout the seasons, I am in love with their maple tequila cocktail – featuring warm syrup poured into the vodka causing it to instantly crystallize and make the drink taste like maple candy.

The Essex House uses local maple syrup in many of their dishes, often in interesting ways. I find this to be one of the restaurant’s signatures.

If you choose to end your evening at the Essex House instead of starting here – their entrée menu has more than a few unique choices. Florentine ravioli or their build your own burger menu are among our favorites. All you can eat Fried Shrimp Wednesdays are popular among locals, as are Taco Tuesdays with margarita specials and Thirsty Thursdays with $1 Bud Light Drafts.

House made Buffalo Dip with crispy wontons from KT Rays restaurant in Island Pond Vermont

On leaving the Essex House, we cross the street and head towards KT Ray’s on the Pond. In the summer, this Island Pond restaurant has the perfect view of the weekly Friday Night Live concerts. Their outdoor patio area is comfortable and right in the middle of things, making for a fun night during the warmer months.

As the second stop on your Adult Dinner Tour, you will have to be careful to not over eat here, as the portions are large and there are so many tempting options on the menu.

We suggest trying the buffalo chicken dip – chicken coated in a house made buffalo sauce and incorporated in a creamy dip with bubbling cheese, served with tortillas. This delicious dip also comes in a wrap, if you are looking for something with a little more substance this would be a perfect option. Also on the appetizer menu are a spinach and artichoke dip and  nachos – both perfect option at this midway stop on your dinner tour.

Delicious burger with blueberry and brie from Island Pond, VT restaurant

KT Ray’s on the Pond features blueberries throughout their menu, bringing a sweet and savory flavor profile to many of their dishes.  So if you happen to stop at KT Ray’s restaurant as the last spot on your tour, or are looking for something a bit more substantial to split with other diners – we suggest trying their signature Blueberry Lane burger.

You have never had a burger like this, with fresh blueberries as the crowning jewel and bubbly brie cheese as an added bonus. The blueberry bacon melt, pasta dishes, or Friday night Prime rib are all dinner entrees sure to fill you up and require a doggy-bag.

A full bar adds another cocktail to the list, or try one of their many draft beers, wines, or a cider.

Leaving KT Ray’s cross the street one more time and head towards the center of town. On your left is Hobo’s Café – authentic BBQ on the Canadian border, what more could you ask for?


I like finishing up our adult dinner tour here because Hobo’s bbq meals come in two portion sizes. Small meals come with only one side and less of the main entrée. After eating at two other restaurants, this is perfect. You can order the option that best fits how full you are feeling.

Hobo’s Café has the best cornbread I’ve ever eaten, with a maple-butter that is divine. The brisket, pulled pork, and the ribs are all delicious, and are all just as good the next day if you have to take some home. Friday nights are fish night with different options based on availability.

baked-beans-coleslaw-cornbread-from-hobo's-cafeIf you decide to start your adult dinner tour here, be sure to order a small meal to split – otherwise you will never have enough room to enjoy the other Island Pond restaurants we have mentioned.

After finishing up your dinner tour, the walk back to the car is a welcome respite, helping in the digestion process. It has been our experience that these dinner tours leave you more full then you’d expect and can be less expensive then eating a full meal with apps and drinks at one place (depending on drink orders and how hungry you happen to be of course).

If you try our Island Pond Dinner Tour, we’d love to hear about it. Post photos to our Facebook page, or message us about it.