Our Osgood’s Donut Dip Across the Border Adventure

worlds largest donut well in real life anywayDH and I recently had an adventure. We went to Osgood’s in West Springfield to get firmer cushions for our downstairs man cave sofa. I was extremely cranky regarding the whole trip. I had other things to do. But I had promised DH new cushions as part of his requested Father’s Day gift, so I got in the car anyway. Did I mention I was very cranky? I tortured him mercilessly with my wifely crankiness for a good solid 45 minutes … until our adventure began to decisively unfold. 

donut dip springfield massachusetts doing business since 1957We had a terrible time getting to Osgoods. The drive normally takes one hour. But to start, there was a backup on the Pike FOR NO REASON. It seems the turnpike crew managers left up signs that the lanes were narrowing to one. But the lanes NEVER EVER did narrow to one. Even so, everyone else on the road began slowing down starting like 30 miles away, anyway. It was extremely beyond annoying. We were both cursing. We are super compatible in this important respect.

donut dip tee shirtEventually, we were beyond the unnecessary bottleneck and off the pike and onto our exit, Exit 3. The next delay:  We we missed a key turn in Westfield. I had chosen this sideways-to-Osgoods route from mapquest. Bad call. That set us back another 20 minutes, but by then we had cast our lots to the wind and were just going with the flow. The day was going to be shot, there was no denying. We were starting to laugh everything off.

Over the river and through the woods, we finally got to Osgoods. Everything went fine there – sort of. We could not get the cushions immediately, because we wanted the very firmest possible, and they had to order them. But, we were taking it all in stride. Guess we’d be making another trip!

donut dip boxBy now we were starving and set out to forage for a place to eat. We thought we might find something old-timey in West Springfield, but we did not. We got dumped onto 91 North, and I started joking we would be eating at Chili’s soon. Sure enough, the first significant exit included signs for Chili’s. We took it. The same sign also indicated a non-chain Mexican place — we were all for that and started getting our enchilada mojo on. But then, we got onto a road where we literally could not turn around for like 8 miles. That’s when we first cruised past Donut Dip, over on the right. But we needed Food first.

donut dip donutsWe finally turned around. We kept looking for the Mexican place, but did not see it. Before we knew it we were in Fast Food and Casual Dining land. Even now we kept making wrong turns. By then I was Starving. I did not Care where we ate. Crap: We missed the turn for Chilis. I yelled at DH, but in a keystone cops we do have fun don’t we i remember why i married you kind of way.

Now we were back on the same road that made us drive 8 miles before we could turn around — the road that went past the Donut Dip. Needing some gratification after 25 minutes of driving in a circle, DH slammed on those brakes, and into the Donut Dip we went. We immediately realized that after surviving at least 4 rings of driving adventure hell, we had been delivered unto: Retro Donut Heaven! at the donut dip

It turns out that Donut Dip is quite the landmark. It makes its donuts on site daily and has third-generation owners. Here is what this political website had to say about it:

It has to be one of the most beautiful signs in America, not for its value as a piece of nostalgia, but as a thing in itself, a series of hot pink letters swirling around shadow, an alliteration made of neon that evokes less the past than another world. As it happens, the sign is easy to reach from the highway, and the donuts are the best in New England, maybe the best in the country.

We promptly slapped down $50 for: one super duper sized donut, a dozen mixed donuts, and three tee shirts — two blue, one pink.

The folks working there were also very nice and told us how to get to the Mexican place — which was RIGHT across the street but tucked back a ways.

Vintage photo from the Donut Dip website

We had to illegally jump the curb and scrape the bottom of the car to turn into the restaurant yet avoid having to drive 8 miles in the wrong direction before we could turn around. Yes, our luck had defiantly turned. It was still early at the restaurant, and we got seated right away. (There was a lineup by the time we finished dinner.) We inhaled super duper delicious enchiladas and the best guacamole ever. We would have mainlined margaritas, too, but we had to drive home.

eating the worlds largest donut he can do it!It was the best day ever. And we had donuts for dessert.


Get our retrolicious free newsletter.


Get our retrolicious free newsletter.


  1. Gavin Hastings says

    First off…..(and I am fully awake today)…You were on Riverdale Street (aka Rt 5). Do you know how many people are seriously injured making U-turns on that stretch??? Be careful…..Do you really want to be a crash victim couple, get duct-taped to a surfboard and then have ME staring down at you in the ER asking very personal questions??? (You know I’d make some up….)

    That said: Donut Dip is a treasure!
    No frozen donuts here. They are like the last donut maker in the area who’s product still has a crunch-y shell. (The oil must be something like thousand degrees…)
    There is another location 10 minutes away from me in East Longmeadow; on the other side of the Ct River…so I am covered!

    ps: Riverdale Street/Rt 5 continues up by Cindy, Pleasant Street Northampton, Yankee Candle in So Deerfield and on to Greenfield without any turns. AND- for old time-y in “West-Side”, try the White Hut…..

    • pam kueber says

      Gavin, how is it that you make a trip to the emergency room sound FUN. We will be careful. Maybe on Tuesday, when we go get our cushions then head to Donut Dip, we will continue on Route 5 all the way into Holyoke just for the scenic tour, and turn around when we can reconnect via I-91 S.

    • Paul says

      You are so right, Gavin. White Hut is a gem. And Donut Dip is terrific. The sight of their little, waxed paper bags can brighten my darkest day.

      My untested place up in Springfield (I’m in West Hartford, CT) is Gus and Paul’s. I have heard good things. What do you say, Gavin and Pam? Any reviews?

      • Gavin Hastings says

        I had some silverwork done by a guy in Providence RI…his only stipulation was that I ship a dozen G&P’s Onion Rolls with my item!!!

  2. brad says

    wow…..i lived in northampton for 12 years and worked in springfield for 20 and somehow i never went to donut dip…..what a dummy i was!!!

    i am going the next time i come up ….

  3. kristen says

    Loved this! Donut Dip is a hop, skip, and a jump from my house the next town over and my kids have come up with a little “poem” to sing every time we drive by -“Ya take a donut, ya dip it, Donut Dip!” (They humor my love of all things retro) We will be making a trip there this week for something “fun” to do 🙂

  4. Cindy says

    Gavin is right…that is Riverdale Rd. and we’ve all been caught in the wrong direction at one time or another.
    I’ve driven by Donut Dip hundreds of times and never stopped in. Shame on me. I plan to rectify that soon and tell them Pam and DH sent me!

    • pam kueber says

      Why doesn’t the great Commonwealth of Massachusetts make some turnarounds… like the ones in NJ? Argh.

      • Gavin Hastings says

        20 years ago- they did add some! Prior to that, it was REALLY “Highway to Heaven” !

        Please change your lunch destination…if you can make it to the White Hut for a hot dog,, you can easily hop over the Memorial Bridge….turn 3 blocks to the left and have a fantastic lunch at The Fort/Student Prince. Very few restaurants like this one anymore.
        Google it, please. Have fun.

  5. MrsWhitney says

    Sounds like a great day! I especially like the retro doughnut boxes. I’m a sucker for old-school packaging…when General Mills re-issued their vintage cereal box designs last year, I bought several and keep refilling them with new cereal. Anything to add to the time capsule decor! 🙂

  6. John Quirk says

    Hi Pam, Donut Dip is great. When you travel to Holyoke via Rt 5 don’t forget to stop for hot dogs at Nick’s Nest!!! My parents used to go there on dates back in the 50’s.

  7. CindyD says

    “What foods these morsels be” – genius! Ya gotta love a place that throws Shakespeare on a donut box. I’m too far away, but know where I’ll stop if I’m ever in the neighborhood!

  8. Jana (Berniecat) says

    How fun! I love to hear about different local family run “treasures” that people discover in their travels. Moving to the south, I discovered what the “hot light” meant for donuts, but now when I travel up north, I know to watch out for the Donut Dip sign!
    P.S. OMG! I have never seen a donut that big in my life! Did DH eat the whole thing?

  9. says

    Oh, I adore good well made and locally made doughnuts, MMM. And they began in 1957, my current year! If we are ever going West, we shall stop for sure.

  10. Heather says

    How fun to see this post! I know Riverdale Rd. very well and I WORKED at the Donut Dip for a year! My 1954 ranch that I’m buying is just down the road a couple miles in Agawam!

  11. JKaye says

    Great post. So much to enjoy — a doughnut the size of a man’s head, the D’s on the box are made out of doughnuts, the Donut Dip building includes a piece of wrought iron, a decoration I really like (but which my husband hates), and great photos of your DH in your retro kitchen. (How did the giant doughnut make it all the way home? Seems like it would have been eaten on the grueling drive back!) Hope the cushions turn out well for the man cave sofa — that’s a lot of cushion to replace.

  12. Elizabeth Mary says

    Sorry to be a day late on this, but that did allow me to read all the posts. I just wish this had been about a year earlier. Why? Well, about a year ago I drove a good friend from North Egremont , MA near the NY border over to West Springfield to pick up her new car at a dealer on Riverdale Rd (which I did not realize was Rt 5, a road I actually knew). We made the same WRONG turn and ended up going all over the place before we stopped in Springfield so she could call the dealer for directions. Those directions took us over the Memorial Bridge, which left me dumbfounded by its beauty. And, we did drive by the Donut Dip a couple of times. After she got her car we tried to find a place to eat and did a few backwards and forwards on that road before we found a place. Sure wish we had known about the White Hut or the Mexican place. But, like your day, ours ended in many laughs and good memories. Next time I am over there I will definitely stop for a donut.

  13. Gavin Hastings says

    Wait….One more please:
    In depicting your adventure on Riverdale Street/Rt 5, you forgot the part about the TWO 2-Lane Rotarys/Turnabouts (with bridges) located within 2 miles of one another.

    In some countrys they are aptly called aTraffic Circus…Circus=Circle in Latin!

    Makes driving “exciting” again…..

  14. Becky P S says

    Oh how I can relate! we have been on quite a few of those trips that Hubby likes to call Photo Safaris! Glad it ended up a good day!

  15. JMo says

    Must agree with everyone here. Love DonutDip…although usually call on the on ein East Longmeadow (Rt 5 can be nutty). Yes to White Hut and yes to the Fort! Had my rehearsal dinner there at the Fort…try the fried cheese. Gus and Paul’s also a special place. Yum.

  16. Bex says

    I’m in Easthampton! (also – were you surprised at how Osgood’s has shrunk? I was shocked last time I went in there…..)

  17. lexavline says

    I just ran across this post (how did I miss it?) and I have to say that you just described the best day ever!

Leave a Reply

Your email address will not be published. Required fields are marked *