Visit all 9 New England Casinos in 7 Days

Many people across the country have visited at least one New England casino. However, NETimeGambling plans to visit ALL 9 New England casinos – in only seven days. So here is your itinerary for a one-week journey in New England, where you can enjoy tourist destinations and gamble for at least four hours in each casino. This is an itinerary to Visit New England’s Casinos in 7 Days – all of them! Starting on any day of the week. Today is New England Casino Trip – Part 1; part one in the three-part series.

The Ground Rules

  • This is a roadmap, not a budget spreadsheet.
  • The cost would vary greatly depending on lodging costs. For example, anyone on a high rewards level might have comped rooms or suites waiting at certain hotel casinos.
  • Flight times for those outside New England could vary greatly. So, on this fantasy trip, we can arrive and stay overnight whenever and wherever we want.
  • This is a pre-Covid, or post-Covid, itinerary. That may be fantasy today, but the itinerary is confirmed every day.

One more thing – the starting location for those of us IN New England could be in any hotel-casino we are staying overnight. Here we gooooooooo…

Visit New England’s Casinos in 7 Days

Day One

Visit New England's Casinos in 7 Days
Bradley International Airport, Windsor Locks, Connecticut.

We start in Hartford (Windsor Locks, actually) after flying into Bradley International Airport. Your rental car is waiting for you, it’s late morning, and it’s time to begin. Our first stop is MGM Springfield, less than 30 minutes away.

New England Casino Trip - Part 1
Inside MGM casino

On arrival, you enter the “industrial chic” ambiance of MGM Springfield. If you don’t have a rewards card, you first sign up for your free rewards card at the players’ rewards desk at every casino property. Now, time for lunch.

TAP is an expansive sports bar with bowling and an arcade in the back. The food is delicious, and the atmosphere and menu are pub-style. Great beer offerings feature local and surrounding state breweries. Two menu suggestions include the Cobb Salad and the Rueben. Bon appetit!

Rest of Day One

The afternoon is set aside for gambling at MGM Springfield. Also, I suggest your first stay over at their beautiful new Hotel. After that, we’re driving to Maine tomorrow, so you need to get some good rest.

Supper? The high price point would be Chandler Steakhouse. For a lower price point – go next door to Red Rose Pizza, a local Springfield gem.

Visit New England's Casinos in 7 Days
Red Rose Pizzeria Springfield, MA

After supper, it’s up to you. More gambling? Maybe a quick trip to Naismith Memorial Basketball Hall of Fame, with more than 40,000 sq. ft. of basketball history. Maybe drinks at the Commonwealth Bar and Lounge? … Nighty-night. Tomorrow, Maine!

Day Two – The “Pine Tree” State

This day includes a lot of driving. So, why not break it up with a bit of sightseeing? We will stop at Portsmouth, New Hampshire, only 2 hours away.

Portsmouth is one of the most vibrant coastal culinary destinations in New England. It’s a city that honors its colorful history, heirloom foodways, and sustainable practices. Portsmouth passionately engages in extraordinary dining experiences with more than 75 walkable restaurants in the downtown area alone. For more information on Portsmouth, click on “Go Portsmouth.”

Depending on how long you wish to stay in Portsmouth, remember that Bangor, Maine, our next casino, is 2.5 hours more.

Rest of Day Two – Visit New England’s Casinos in 7 Days

We arrive in Bangor, Maine, home to lumberjack Paul Bunyan. He stands 31 feet tall over Main Street and across our destination – Hollywood Bangor Casino and Hotel.

New England Casino Trip - Part 1
Hollywood Casino on the right, with Hotel in the back parking garage to the left.

Hollywood is the smallest casino in New England. Bought and still owned by Penn National since 2005, it offers craps, roulette, blackjack, and High Card Flush. A small floor of slots and a poker room round out its offerings. It’s also a racino with in-season harness racing.

Check into the Hotel first. It is a small hotel, and the rooms are smaller than usual. However, they come with all the amenities, are very clean, and the service is exceptional.

I have four suggestions for supper – all low to medium price points.

  • Hops House 99 – (Inside Hollywood) 99 different brews feature local drafts, delicious pub food like burgers and sandwiches, and big games on TV. Entertainment on the weekends.
  • Epic Buffet – (Inside Hollywood). If you prefer a buffet, it does the trick.
  • John Geaghan Restaurant & Pub – Next door
  • Sea Dog Brewing Company – a lovely walk along the riverwalk behind Hollywood brings you a great beer, a beautiful view, and great seafood.
  • The fine dining we suggest is Novio’s Bistro.

After supper, the casino is ready for your inspection and play. This is the only non-24-hour casino in New England. It opens at 8:00 am and closes at 3:00 usually am.

Tomorrow, we travel SW to Maine’s other casino.

Day Three – Oxford Casino Hotel

Get an early start to drive to our third casino in Oxford, Maine. It’s the Oxford Casino Hotel. It has expanded its casino floor, which is only nine years old, added more dining, and now has a new hotel. The rooms are beautiful; the casino floor is usually crowded, and the property is located in a very remote area. Grab lunch at the Ox Pub in between your four-hour gambling spree.

A possible change to the itinerary would be to swap days with the two Maine casinos. Either way, you’ll have time to experience both small casinos, enjoy good hotel stays, and be ready to arrive at the next stop. Then, it’s off to Boston, Ma., Everett, to be exact. Time to explore Encore Boston Harbor.

Encore Boston Harbor – Day Three

After an enjoyable time at Oxford Casino Hotel, it’s shoving off to Boston. The most recent casino to be built in New England is owned by Wynn Resorts and could be considered New England’s jewel. Encore Boston Harbor is located 2.5 hours from Oxford, minutes north of Boston.

New England Casino Trip - Part 1
View from South Lawn

By this time, you know the drill – hotel check-in and rewards club—next, supper.

Food is pretty pricey in this place, but you get what you pay for. The cuisine is outstanding. This is the place to make reservations for a quality meal. Rare Steakhouse and Red 8 are the recommendations. The buffet is fantastic, but it might not be open.

  • Courtesy of Encore Boston Harbor

Then, it’s gambling until bedtime. There are also plenty of chances for people-watching and enjoying the extravagant decor inside and out. The gardens and harbor walk outside is a must – if not at night, definitely in the morning before leaving.

Get Ready For Part Two

That’s Part 1 in the series. I hope you’re not too tired. Part 2 finishes with Massachusetts and all of Rhode Island. Part 3 ends our journey in Connecticut for the last two days. Check in tomorrow for Days 4 & 5!