Adult Dinner Tour #1 – Island Pond

By: Tabitha Armstrong | 09.30.18

Friday Night Live Event in Island Pond 2018Updated May 25, 2019

The 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 both restaurants, take a picture of all three showing the restaurant name and the date – dates between June 1 and Sept. 30 2019 qualify – 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.

Maple cocktail from the essex house tavern in Island PondWe love starting our Adult Dinner here because they have the perfect appetizer menu.

Stuffed 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.

The 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.

Lobster-roll-with-fries-and-slaw-from-restaurant-in -Island-Pond-VT

Summer time brings their delicious lobster roll, which finds its way to the specials menu off and on all season. This is one of our absolute favorite items, and is one of the best lobster rolls I have ever eaten!

Large chunks of fresh lobster are very lightly dressed and tossed in lemon juice and seasoning. Then, melted butter is poured into a toasted bun before being filled with the meat. Absolutely fantastic!

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.

Island Pond features a number of town wide events every year and these bring special wine tastings at the Hearth and Home Country Store, food trucks, vendors, and other culinary treats besides the year round restaurants, adding to the overall adult dinner experience.

One of these weekly, summer time events is their weekly Friday Night Live. Leaving the Essex House puts you right across the street. We typically enjoy the music for a while, letting food settle before heading off to our next stop – Hobo’s Café.


Just down the street from the Essex House, you can enjoy delicious, authentic BBQ slow cooked to perfection.

Dining, live music, and BBQ – 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.

slow-cooked-brisket-from-Hobo's-Cafe-Island-PondIf 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.