Adult Dinner Tour #1 – Island Pond

By: Tabitha Armstrong | 09.30.18

Friday Night live concerts in Island Pond vtUpdated June, 2022

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 many restaurants, live music, town wide celebrations for holidays, and town activities to keep the community involved have filled area social calendars all year long.

The culinary offerings are all the more wonderful because they are in walking distance from one another, meaning you can enjoy an adult dinner, sampling items from each location for a truely memorable dining experience.  (What is an ‘adult dinner’?)


Take the Island Pond Dinner Tour

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

stuffed mushrooms from Essex House and Tavern in Island Pond VTIsland Pond, Vermont 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. And, their outside dining space is a wonderful way to enjoy Vermont evenings.

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, pretzle bread sticks, 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.
An assortment of sandwiches, including a Roast Beef French Dip;  their broiled scallops baked in a maple bourbon compound butter, or their Thai Vegetable rice bowl with a number of different protein choices are our among our favorites.

Island Pond features a number of town wide events every year and these bring food trucks, vendors, and live music to the area, adding to the overall adult dinner experience. By far the best is Friday Night Live! This outdoor, free, weekly music event has made Island Pond a destination for many summers. Though they had to pause the event through the last two pandemic summers – it is back, and the area is excited for the summer line up. (Check out the calendar)

Leaving the Essex House we typically head across the street to the Kingdom Grill.

Here you will find a full bar with an assortment of cocktails. We enjoy their chicken sliders, a nice light alternative to a bigger burger. The fried chicken sliders have a seasoned batter and are fried crispy. They are served with your choice of their house made mustards. They make for a great option on an adult dinner evening because they don’t take up too much room in your belly.

This location also has an extensive burger, and specialty hot dog menu making it perfect or family dinners with kids.

From here we head up the street 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.

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.

Also available in Island Pond is Cucina di Gerardo – a wonderful Italian restaurant. They offer a few inside seats and take out. On adult dinner nights we normally don’t make it here because the food is so hearty. But their mussles, calamari, or the eggplant rolletini offer a few appetizer options that won’t make you too full and are perfect fits for this dinner tour.

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.


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